Major League Real Estate Podcast

PODCAST · business

Major League Real Estate Podcast

The Major League Real Estate Podcast is the show for operators and sponsors who compete at the highest level. We dive deep into the journeys, investing frameworks, and tax strategies of elite portfolio builders, all while spotlighting these playmakers who build and scale multi-million-dollar portfolios. Whether you're syndicating deals, managing large assets, or scaling partnerships, you’ll hear firsthand how top performers get it done. We explore every strategy related to acquisitions, operations, and exits and break down the best ways to optimize your taxes for each one. Tune in for real stories, sharp insights, and proven frameworks you can use right now.

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    41. S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make

    Should your real estate syndication use an S corporation, a C corporation, or an LLC taxed as a partnership? In this episode, Thomas Castelli and Nathan Sosa break down the real tax implications behind entity structuring for syndicators, fund managers, and passive investors. They explain why LLCs taxed as partnerships are typically the gold standard for real estate syndications, where S corps can accidentally limit depreciation benefits, and how C corps can create double taxation problems that investors often overlook. You’ll also learn: - Why depreciation and debt allocation matter so much in syndications - The hidden limitations of S corps for real estate investors - When a C-corp blocker actually makes sense - How GP entities and management companies should be structured - The biggest mistakes syndicators make before raising capital Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    40. Why 1031 Exchanges Break in Syndications (And How to Work Around It)

    In this episode of the Major League Real Estate Podcast, we break down everything you need to know about 1031 exchanges and why they get complicated fast when syndications are involved. We cover: - Why you can’t directly 1031 into a syndication - The biggest issues GPs and LPs run into when trying to defer taxes - Workarounds like Delaware Statutory Trusts (DSTs) and Tenants-in-Common (TIC) structures - Advanced strategies like drop-and-swap and how to plan for them on the front end - Common pitfalls including boot, debt replacement, and IRS scrutiny We also cover practical advice for syndicators, like how to structure deals upfront if you want to offer 1031 optionality, and what investors should look for when trying to defer gains into their next opportunity. Whether you're an active investor, passive LP, or syndicator, this episode will help you understand how to properly navigate 1031 exchanges without blowing up your deal or your tax strategy. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    39. K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game

    In this episode, we’re breaking down one of the biggest misconceptions in real estate investing: the idea that you need to rush to file your taxes by April 15. If you’ve ever felt pressure to get your K-1s out early, file on time, or keep investors happy by hitting arbitrary deadlines, this episode is for you. We discuss why tax extensions are not only normal in the world of real estate syndications and funds, but often the smarter move. Rushing the process can lead to costly mistakes, amended returns, and unnecessary headaches for both operators and investors. You’ll learn how to properly set expectations with your LPs, why accuracy matters more than speed, and what really happens when you file without complete information. We also cover key lessons from this tax season, including common misunderstandings around bonus depreciation, passive losses, and how income from things like high-yield accounts can create unexpected tax implications. Plus, we walk through what you should be doing right now, post tax season, to review your returns, improve your processes, and plan ahead for the rest of the year. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    38. Carried Interest: What’s Really Behind the "Loophole" and Why It’s Misunderstood

    In this solo episode, Nate Sosa breaks down one of the most important — and most misunderstood — concepts in real estate syndication: carried interest. From its surprising origins in 16th-century shipping voyages to its modern-day use in private equity and real estate deals, Nate walks through how carried interest actually works, why it exists, and how it’s taxed. You’ll learn: - How GP/LP structures and waterfall distributions work - The difference between promote, profits interests, and equity - Why carried interest is taxed at favorable rates - The real risks GPs take (and why the upside exists) - What Congress has tried (and failed) to change about it - Common structuring mistakes that could trigger IRS issues Whether you’re an active sponsor or passive investor, this episode will help you better understand deal economics and what to watch for when evaluating opportunities. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    37. Why Multifamily Is Still Uninvestable (And Where Smart Money Is Going Instead) With Brian Burke

    Brian Burke, CEO of Praxis Capital and author of The Hands-Off Investor, joins the show to break down the current state of real estate investing and why he believes multifamily is still too early to touch. We discuss: - Why the multifamily market looks like a “traffic collision” right now - The biggest mistake investors make trying to time the bottom - Why senior housing may be the most overlooked opportunity today - The real impact of AI on real estate (and jobs) - Why tax benefits should NEVER be your primary investment thesis If you’re an LP or GP trying to navigate today’s uncertain market, this episode will help you think more strategically about timing, risk, and where the real opportunities are emerging next. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    36. Disguised Sales: How Refinances Can Trigger Unexpected Taxes in Syndications

    In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa break down one of the most misunderstood areas of partnership tax law: disguised sales. While many investors assume distributions and refinance proceeds are tax-free, the rules change when partnerships and contributed property are involved. Get it wrong, and what you thought was a tax-free event could actually be treated as a taxable sale. You’ll learn: - How partnership distributions actually work (and how they affect your basis) - What a disguised sale is and why the IRS cares - The 2-year rule that can trigger unexpected taxes If you’re a syndicator, GP, or investor contributing property into deals, this episode is a must-listen to avoid costly tax mistakes. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    34. Flying Private: What Syndicators Should Know About Deducting a Jet

    In this episode, Nate and Tom break down the truth behind private jet tax write-offs: what works, what doesn’t, and where investors get into trouble. They dive into how bonus depreciation can create significant tax savings, why most jet structures default to passive losses, and how rules like material participation, business use, and grouping elections can make or break your strategy. Plus, they walk through real tax court cases where investors lost and what you can learn from them. If you’ve ever considered buying a jet (or just want to understand the strategy), this episode will help you avoid costly mistakes and stay on the IRS’s good side. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    33. K-1 Season Explained: Depreciation, Capital Accounts, and Passive Losses

    K-1 season can be confusing for real estate investors, especially when depreciation, passive losses, and capital accounts start showing up on your tax documents. In this episode, Nate and Tom break down the fundamentals of depreciation in real estate partnerships and how it impacts both general partners (GPs) and limited partners (LPs). They walk through how cost segregation studies accelerate deductions, why passive losses matter for investors, and how depreciation is allocated inside syndications. They also explain why capital accounts and outside basis determine whether investors can actually use the losses shown on their K-1 and why partnership operating agreements need to align with IRS rules like Section 704(b). Whether you're a syndicator structuring deals or an investor trying to understand your K-1, this episode provides a clear overview of how depreciation works inside real estate partnerships. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    32. How to Survive the 2026 Real Estate Cycle: AI & Capital Raising Strategies with Victor Menasce

    In this episode of the Major League Real Estate Podcast, we sit down with Victor Menasce, tech executive turned real estate developer, host of the Real Estate Espresso Podcast, and author of Magnetic Capital, to break down what’s really happening in today’s market. From leaving Silicon Valley in 2009 to building multifamily projects in uncertain cycles, Victor shares how his background in tech shaped the way he approaches development, capital raising, and long-term wealth building. But that’s not all. Victor also dives into: - Why the real estate market is “splitting in two” and who gets squeezed - The biggest mistake syndicators make when raising capital - What lenders are doing behind the scenes (including term sheet bait-and-switch tactics) - Why real estate should be treated like product design, not a commodity For GPs raising capital, LPs evaluating deals, or operators trying to adapt to a rapidly changing market, this episode delivers strategic insights on surviving — and thriving — in the 2026 real estate cycle. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: https://go.therealestatecpa.com/question Connect with Victor: https://ystreetcapital.com/ The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    31. The Syndication Mistakes I’d Never Make Again with Thomas Castelli

    In this episode of the Major League Real Estate Podcast, Thomas Castelli shares the full story of his journey, from attending local RIAs and investing as an LP, to joining the GP team on an 82-unit apartment complex, navigating hurricane due diligence, raising capital under pressure, and exiting during the chaos of COVID in 2020. But that’s not all. Tom also opens up about: - The hardest lesson he learned about capital raising - Why most new GPs underestimate the importance of investor relationships - What changed in the syndication world since 2017 - The risks LPs don’t think about (until it’s too late) - How a failed ATM investment reshaped his investing philosophy -,Why experience matters more than ever in today’s market For GPs raising money, LPs evaluating risk, or investors entering the syndication space, this episode shares practical, experience-backed insights. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    30. From 19 Units to 2,700: Scaling Syndication and Surviving the Rate Shift with Jens Nielsen

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Jens Nielsen of Open Doors Capital to break down how he went from a 25-year IT career to full-time real estate and scaled from buying a couple of fourplexes to investing in 2,700+ multifamily units as a GP. Jens breaks down: - How he went from 0 to 19 units in year one and built momentum from there - The pros/cons of joint ventures vs. syndications, including flexibility, cost, and incentive alignment - The operational metrics he watches most (occupancy, collections, rent growth, reimbursements, and expenses) - The hard lessons from the rate shift: bridge debt, underwriting assumptions, and mechanical systems Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    29. Partnership Audit Guide

    Nathan and Matt dive into one of the most anxiety-inducing topics in real estate tax: IRS audits—specifically what a partnership audit actually looks like and how it differs from individual audits. They break down why partnership audits are far less common than most operators assume, how the current partnership audit regime works, and what really triggers IRS scrutiny. The conversation focuses on practical risk analysis, not fear-based hypotheticals, with real-world examples from years of working with partnerships and investors. Nathan and Matt cover: The most common IRS notices partnerships and individuals actually receive Why partnerships historically haven’t been audited often—and what changed under the BBA regime How partnership audits work today and when tax can be assessed at the entity level The role of IRS divisions, experience gaps, and ROI in audit selection Why low audit risk does not justify indefensible tax positions How to think about tax strategies through a risk-and-reward lens Real examples of aggressive strategies gone wrong, including conservation easements They wrap with a clear takeaway: audit risk should never drive tax decisions. Good tax planning assumes scrutiny, weighs risk intentionally, and focuses on positions that can be defended—not just benefits that look good on paper. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction.

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    28. Year End Checklist: Your Guide to a Smooth Tax Filing Season

    Nathan and Matt shift gears for a practical, nuts-and-bolts episode focused on year-end planning and what operators should be thinking about now to set up a smooth tax filing season. They walk through the key tax, accounting, and logistical items that tend to create friction during tax season—and how addressing them proactively can save time, reduce stress, and avoid last-minute surprises. From entity-level considerations to investor reporting and bookkeeping cleanup, the discussion is geared toward real-world execution, not theory. Nathan and Matt break down: What tax items to evaluate before year end, including income acceleration or deferral, depreciation planning, and credit opportunities Common accounting cleanup issues that slow down tax prep, such as unreconciled accounts, misclassified expenses, and incomplete fixed asset schedules What documents and data you should be gathering now to avoid bottlenecks once tax season hits How investor counts, capital activity, and ownership changes impact timelines and reporting complexity Why coordination between operators, bookkeepers, and tax advisors matters more at year end than any other time of the year Simple process improvements that make future tax seasons easier—not just this one They close with a straightforward message: tax season is rarely stressful because of taxes themselves—it’s stressful because of disorganization and late decisions. Thinking through these items before year end puts you in control, shortens turnaround times, and sets your business up for a clean start to the new year. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    27. Solar Tax Credits in CRE: Real Opportunities vs. Risky Schemes

    Nathan starts by unpacking the difference between deductions and credits, then walks through how the 30% Investment Tax Credit (ITC) works when you install solar on commercial properties—plus how bonus depreciation layers on top of the credit under today’s rules. He explains why the Inflation Reduction Act boosted solar, what’s changing over the next few years, and where engineering studies come into play as project sizes grow. Nathan and Matt break down: How a 30% solar ITC actually shows up on your tax return versus a regular deduction Why you can still get significant bonus depreciation and the credit, and how the 50% reduction rule works in practice The real cost of implementation—equipment, engineering, and making sure projects meet the technical requirements Common “solar scheme” structures where a promoter sits in the middle, finds customers, and promises you credits and losses Why having a management company or middleman usually makes your income and losses passive, limiting your ability to offset active income The material participation rules, and why simply “logging 100 hours” in a paper log isn’t enough in an IRS audit Why the investment itself still has to make economic sense—cash flow, operations, and returns—before you even factor in the tax benefits How solar and other credit structures compare to more established models like low-income housing and historic rehab deals using partnership flip structures They close by emphasizing a simple principle: don’t let the tax tail wag the economic dog. Used correctly, solar and other credits can be powerful tools for CRE operators to enhance returns, build a bank of passive losses, and fund tougher deals. Used sloppily—or purely for tax savings—they can become high-risk audit bait. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    26. Pilots, Paychecks, and Passive Income: The Turbine Capital Playbook

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Tait Duryea of Passive Income Pilots and Turbine Capital to unpack how he’s helping airline pilots and other high-earning professionals turn strong W-2 income into real wealth through passive investing in commercial real estate, oil and gas, and other private deals. Tait shares how he grew up in a multigenerational aviation family, became a major airline pilot in his early 20s, and used that career as a launchpad for investing—starting with a single-family house in Las Vegas and eventually scaling into LP positions across the country and multiple asset classes. Tait breaks down: The gap between high pilot incomes and real wealth-building—and why a big paycheck plus index funds often isn’t enough How he went from a Vegas rental and small multifamily to investing passively in dozens of syndicated deals Why he launched Turbine Capital and the Passive Income Pilots podcast as an education-first, pilot-focused investing platform How Turbine structures deals—fund-of-funds, co-GP roles, and negotiating better economics for LPs while partnering with best-in-class operators His approach to protecting friends-and-family capital through deep sponsor relationships, rigorous underwriting, and outside experts Tait closes by explaining why Turbine Capital is built first as the vehicle he wants his own money invested in—and how serving a niche LP base with education, alignment, and institutional-level diligence creates a durable platform for both investors and operators. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    25. Cost Segregation for Syndicators: From 39 Years to Year One with Edward Griffith

    In this episode of the Major League Real Estate Podcast, Nathan and Matt sit down with Edward Griffith of Hall CPA to demystify cost segregation for large CRE operators, fund managers, and syndicators—and how to turn engineered studies into real cash flow and tax advantages. Edward shares how his engineering background and 15+ years in property analysis and cost segregation led him to run the cost seg department at a large national firm before joining Hall to build out its in-house team. He explains what a cost segregation study actually is, how it accelerates depreciation using shorter asset lives, and where bonus depreciation and QIP still create meaningful opportunities. Edward breaks down: - How cost segregation works in plain English—turning “one building over 39 years” into multiple asset classes you can depreciate much faster - Why bonus depreciation still matters in today’s landscape and how it applies differently to short-term rentals, industrial assets, and other property types - Key rules and timelines around binding contracts, placed-in-service dates, and renovations so you don’t miss bonus or accidentally double count assets - How the component election and qualified improvement property (QIP) can fit into your overall tax strategy - The step-by-step cost seg process for new construction vs. acquisitions—from plans and takeoffs to site inspections and the final report your CPA actually uses - Why on-site visits and engineering-driven reports matter more under the updated IRS Audit Technique Guide - What makes a strong cost seg candidate: site improvements, parking, and why apartments, offices, RV parks, and golf courses often outperform “plain vanilla” warehouses - How to think about land value allocations using appraisals and property tax records instead of arbitrary rules of thumb - Edward closes by emphasizing that cost segregation isn’t just a tax trick—it’s a strategic tool. Done right, it helps sponsors generate losses for investors, sharpen their capital-raising story (“What losses do I get in year one?”), and stay on the right side of the IRS with thoroughly documented, engineering-backed studies. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    24. CRE Insurance 101 for Operators: Protecting NOI with Skylar Romines

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Skylar from ATW Advisors to unpack how large CRE operators and syndicators can turn insurance from a deal-killing expense line into a strategic lever for protecting NOI and keeping closings on track. Skylar shares how she spent 17 years as a commercial insurance broker serving real estate owners and developers before launching ATW as an owner’s rep and outsourced “CRO” for risk and insurance. She explains why she left the brokerage world, how ATW benchmarks programs across the country, and what sophisticated sponsors are doing differently to control premiums across entire portfolios instead of shopping one-off policies. Skylar breaks down: - Why insurance has become the fastest-growing expense line item in CRE and how 50–100%+ premium jumps can blow up deals at the closing table - What’s really behind the recent hard market—replacement cost inflation, supply chain, labor, and reinsurance—and why a “softer” market doesn’t mean you can relax - How portfolio-level strategy, data, and benchmarking beat chasing one-off quotes when you’re renewing across dozens of assets - The liability squeeze in U.S. multifamily: crime scores, Fannie/Freddie requirements, and exclusions (assault & battery, firearms, animal bites, subsidence, and more) that can quietly wreck your coverage - Why geography, crime, and local risk quirks (wildfires, hurricanes, tornadoes, mine subsidence, etc.) need to be underwritten up front—especially when you’re going out-of-market - Practical ways operators are using technology—robot dogs, license plate readers, and other tools—to change the risk story they take to underwriters - When to bring in an insurance advisor in the deal cycle (LOI, PSA, renewal) so your lender and carrier don’t surprise you at the eleventh hour Skylar challenges operators to treat insurance with the same intentionality as debt and tax strategy: know your underwriters, understand your exclusions, review programs regularly, and either become your own advocate—or hire one—so you can protect NOI and keep deals alive in the next hard market. Request a free discovery meeting: go.therealestatecpa.com/mlre Connect with Skylar: https://atwadvisors.com/connect Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    23. How to Scale Your Syndication Business: Systems, People & Processes That Work with Josh Lurie

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Josh Lurie of F Street to unpack how he’s helped scale a boutique real estate investment firm into a multi-market syndication platform built on systems, people, and trust. Josh shares his path from CPA and M&A attorney to joining F Street and building out its investment arm over the past seven years. He explains how the firm sources deals, manages investor relationships, and creates the operational structure needed to grow without losing the personal touch. Josh breaks down: - How F Street expanded from Milwaukee-focused deals to operating across multiple states and asset classes - The systems and processes behind managing deal flow, critical dates, investor communication, and internal operations - Why deal quality drives capital raising and how they match the right investors to the right opportunities - The challenges of educating new investors on real estate vs. private credit - How scaling requires evolution in team structure, communication, and oversight - Why trust, transparency, and long-term relationships are the foundation of their business Josh closes by emphasizing that real estate success isn’t built overnight. It comes from consistency, strong operations, and surrounding yourself with the right people: mentors, partners, and investors. Request a free discovery meeting: go.therealestatecpa.com/mlre Connect with F Street: https://fstreet.com/ Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    22. From $700,000 to $130 Million: How to Play the Long Game with Scott Lurie from F Street

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Scott Lurie, founder of F Street, to unpack how he turned $700,000 into over $130 million of deployed capital and what it really takes to build wealth that lasts. Scott dives into his 20-year journey from fixing and flipping single-family homes to creating a diversified alternative investment platform spanning multifamily, industrial, and private credit. He explains how F Street structures its deals, attracts investors, and scales responsibly while maintaining personal relationships at every stage. Scott walks through: - How he scaled from fix-and-flips to managing over $130 million in private credit and real estate investments - The key differences between multifamily, industrial, and private credit verticals and how each serves a different investor mindset - Why simplicity and trust are the most powerful tools in raising capital - The psychology behind investor loyalty and how consistent monthly payments build long-term confidence - How social media (especially Meta and Instagram) has become a leading channel for investor outreach - The systems and team structure behind managing hundreds of investor relationships - What “playing the long game” really means in business, investing, and relationships Scott wraps up by reminding listeners that real estate success isn’t built overnight. It’s earned through discipline, transparency, and an unwavering focus on delivering results for investors. Request a free discovery meeting: go.therealestatecpa.com/mlre Connect with F Street: https://fstreet.com/ Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    21. How to Factor Taxes into Syndication ROI: What Every Capital Raiser Should Know

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton explain one of the most overlooked areas of real estate syndication: how to accurately factor tax effects into ROI projections and communicate those expectations to investors. Nathan and Matt walk through: - Why syndicators should include tax impact in their ROI calculators and how it changes investor outcomes - The role of bonus depreciation and cost segregation in driving year-one tax losses - How leverage can dramatically amplify those tax losses (with back-of-the-napkin math examples) - The major differences in tax treatment across asset classes like multifamily, industrial, and RV parks - Why state tax exposure matters when investing outside your home state - How to use cost segregation studies effectively and when to get them done Nathan and Matt wrap up by emphasizing that taxes are the “cherry on top” of a strong deal, not the driver, but understanding them can make or break investor trust. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Get the Year-End Tax Checklist: https://go.therealestatecpa.com/4nEUkJM The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    20. Can You 1031 Exchange Into A Syndication? (And Why It's Usually Not That Simple)

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton unpack one of the most complex topics in real estate investing: how 1031 exchanges interact with syndications and TIC (tenants-in-common) structures, and why it’s rarely as simple as investors think. Nathan and Matt walk through: - The key difference between a 1031 exchange and an investment into a syndication - Why partnership interests don’t qualify for 1031 treatment (and what does) - How TIC structures can allow investors to roll 1031 proceeds into a deal - The IRS’s “if it quacks like a duck” rule and what it means for structuring ownership - Common pitfalls when trying to 1031 into a fund or LLC - The drop-and-swap strategy: how it works and why it’s full of gray areas - What IRS guidance Revenue Procedure 2002-22 requires for a valid TIC structure - Why getting both a CPA and a tax attorney involved early can save major headaches - How syndicators can evaluate when a TIC arrangement actually makes sense Nathan and Matt wrap up by emphasizing that while 1031 exchanges can be a powerful tool for real estate investors, combining them with partnerships or syndications demands expert guidance. Understanding these nuances helps operators close deals confidently, protect investors, and stay compliant with IRS rules. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    19. Every GP Needs to Know This: How to Turn Passive Income Into a Real Advantage

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton unpack one of the most misunderstood topics in real estate investing, the difference between active and passive income and how GPs can turn that knowledge into a true advantage for their investors. Nathan and Matt walk through: - The key distinctions between active and passive income and why it matters for tax strategy - How the 1986 Tax Reform Act changed real estate investing forever - Why real estate losses are usually passive (and when they’re not) - How GPs can educate investors on what their K-1 losses actually mean - The concept of a “Lazy 1031 Exchange” and how it mimics a traditional 1031 - How passive losses can offset passive gains, and the one scenario where they can offset active income - Why suspended passive losses are never wasted and how they carry forward - How understanding these rules can help GPs raise more capital with confidence Nathan and Matt wrap up by emphasizing that mastering these tax distinctions isn’t just for CPAs. It’s a must for every syndicator who wants to build credibility, attract smarter investors, and structure deals that deliver both returns and real tax benefits. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    18. The K-1 Problem: Why Investors Wait (And How to Fix It)

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton dive into the realities behind “The K-1 Problem” — why investors often wait months for their K-1s and what syndicators can do to fix it. Nathan and Matt walk through: - The real reason K-1s take so long to prepare - Why accurate and timely bookkeeping matters more than you think - How poor communication between GPs, investors, and CPAs slows down filings - The role of partnership tax returns (Form 1065) and what “getting K-1s out” actually means - Common misconceptions about extensions and whether they increase audit risk - Best practices for getting financials ready by March 15th They also share practical strategies to streamline the process, from maintaining up-to-date investor information to giving your CPA read-only portal access. Nathan and Matt close by emphasizing communication, realistic expectations, and proactive planning as the keys to faster filings and stronger investor relationships. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    17. How Techvestor Scaled STR Syndications to 150+ Rentals (OpCo/PropCo, Data & More)

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton sit down with Sief Khafagi and Corbin Weinerman, from Techvestor, to unpack how they scaled from tech careers into one of the most innovative short-term rental syndications in the industry, growing to 150+ STRs and pioneering a data-driven “mini-resort” model that’s redefining investing. Nathan, Matt, Sief, and Corbin dive deep into: - OpCo + PropCo 101: how splitting operations from asset ownership turbocharges scale, reduces risk, and protects GP promote economics - The data-driven acquisition playbook: filtering 35,000 listings down to a handful of true comps and why 5+ bedroom “group homes” are the most under-served segment in STRs - Building a product, not just a property: how Techvestor creates destination-grade homes with pickleball courts, bowling lanes, mini-golf, and even lazy rivers to dominate demand and pricing power - Raising capital like a startup: why investor experience, branding, and 24/7 transparency matter more than ever in today’s competitive capital markets - Post–Big Beautiful Bill strategy: how bonus depreciation tailwinds have supercharged demand for turnkey STRs and reshaped their acquisition and disposition plans They also share hard-earned lessons on navigating contractor disasters, scaling teams with Silicon Valley-level talent density, staying ahead of Airbnb algorithm changes, and managing investor relations through volatile markets. Whether you’re an experienced sponsor, aspiring GP, or STR operator looking to level up, this conversation is a masterclass in building a resilient, scalable, and tax-efficient investment business. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Connect with Techvestor: https://www.techvestor.com/ The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    16. The Syndicator’s Growth Playbook: Tax Strategy, Partnerships, and Non-Correlated Investing

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton are joined by Patrick Grimes, engineer-turned-syndicator and founder of the Passive Investing Mastery Series, to unpack how he scaled from single-family BRRRRs to co-GPing 2,000+ multifamily units and expanded into non-correlated alternatives like first-position debt and litigation finance. Nathan, Matt, and Patrick discuss: - The “tax trifecta”: S-Corp optimization, R&D tax credits, and bonus depreciation working together - How Patrick documented hours to achieve Real Estate Professional (REP) status and why timing your W-2/contractor mix matters - Moving from DIY to partnerships: underwriting like an engineer, avoiding analysis paralysis, and learning to “fire yourself” - Why non-correlated alts (debt funds, legal/medical) can stabilize portfolios when real estate cycles hit turbulence They also cover lessons from the subprime reset to today’s multifamily headwinds, how accredited investors approach allocation beyond the 15–25% real estate band, investor profiles and reinvestment rates, and practical tax angles like 1031s inside funds and little-known 1033 exchanges for casualty gains. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] Connect with Patrick: https://passiveinvestingmastery.com/ The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

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    15. QOZs and QOFs Explained: Expert Lessons from $100M+ in Deals with Barrett Linburg

    In this episode of the Major League Real Estate Podcast, Nathan Sosa is joined at the 2025 Tax, Legal, and Wealth Summit by Barrett Linburg, Managing Partner at Savoy Equity Partners, to dig into the real-world strategies, structures, and tax benefits of Qualified Opportunity Zones (QOZs) and Qualified Opportunity Funds (QOFs). Nathan and Barrett discuss: - How Barrett went from an 8-unit rehab in 2012 to managing $100M+ of OZ equity - The unique two-tier structure of QOFs and QOZBs, and why paperwork precision matters - Why OZ projects align with long-term, community-focused investing - Lessons learned from OZ 1.0 and what’s changed in OZ 2.0, including permanency and new rules for rural tracts They also cover how to evaluate census tracts and identify the “path of progress,” how to manage the substantial improvement test, the myths about 10-year lockups, and why sticking to plain-vanilla real estate deals often produces the best OZ outcomes. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  27. 15

    14. What Happens When a Partner Sells Their Interest? Tax Implications Explained

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton break down the complexities of Section 754 elections and why they matter for real estate partnerships. Nathan and Matt walk through: - What happens when a partner sells or redeems their partnership interest - How tax basis works in partnerships compared to direct property ownership - Why disparities arise between fair market value and partnership book value - The role of Section 754 elections in resolving those disparities - Key differences between Section 734 and 743 elections - The pros, cons, and long-term operational impacts of electing 754 They also explore practical considerations like appraisal costs, capital account adjustments, and the “flavor of income” effect that can make elections highly valuable in some cases but burdensome in others. Nathan and Matt close with insights on how syndicators and investors should evaluate these elections with their CPA to balance investor fairness, compliance, and long-term strategy. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  28. 14

    13. Section 754, Refinance Distribution, And Top Partnership FAQs

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton answer real-world tax questions from listeners in their first Partnership Tax Mailbag session. From Section 754 elections to refinance distributions, they break down complex rules syndicators need to understand to protect both themselves and their investors. Nathan and Matt walk through: - What a Section 754 election is, why it matters for new investors, and when to include it in your operating agreement - The long-term implications of making the election, including step-ups, step-downs, and being locked in for future adjustments - How refinance proceeds and return of capital impact investor tax liability - Distribution considerations when some investors use retirement accounts (IRAs/401(k)s) and others invest personally If you’re raising capital, structuring syndications, or navigating partnership tax complexities, this episode delivers practical answers to questions you or your investors are likely asking. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  29. 13

    12. The Truth About Drop and Swaps: Timing, Costs, and Case Law with Brandon Hall

    In this episode of the Major League Real Estate Podcast, Nathan Sosa is joined by Brandon Hall, CPA, CEO and Founder of Hall CPA, to break down the tax and legal complexities of drop and swaps, a strategy used when partners in a real estate deal want to go their separate ways while still pursuing 1031 exchanges. Nathan and Brandon discuss: - What a drop and swap is and how it differs from a standard 1031 exchange - Why timing and documentation are critical to surviving IRS and state scrutiny - The recent New York court case that upheld a same-day drop and swap - The role of operating agreements, 1031 clauses, and attorney involvement They also cover the real costs of running a drop and swap, how poor fact patterns can sink a case, and why business intent and solid legal groundwork remain the strongest defenses in complex real estate transactions. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  30. 12

    11. Why 1031 Exchanges Get Messy in Partnerships and Syndications

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton dive into the complexities of 1031 exchanges and why they can be both powerful and problematic for real estate syndicators. Nathan and Matt walk through: - What a 1031 exchange is and how it works as a tax deferral strategy - The 45-day identification rule, 180-day closing window, and the role of qualified intermediaries (QIs) - Why 1031s are straightforward for individual investors but difficult to execute in syndications - How raising capital and bridging equity gaps can create taxable gain events - The impact of rolled-over basis on depreciation and cost segregation benefits - Why Tenancy-in-Common (TIC) structures are often used to bring 1031 investors into syndications and the risks if they’re not structured correctly - How failed 1031s can still create planning opportunities depending on timing Real-world scenarios where syndicators must balance investor expectations, compliance requirements, and long-term tax strategy They also highlight the legal, tax, and investor relations challenges syndicators face when attempting 1031s, and why working with an experienced CPA or tax advisor is essential to avoid costly mistakes and missed opportunities. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: [email protected] The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  31. 11

    10. Qualified Opportunity Zones: Structuring Funds and Raising Capital

    In this episode of the Major Real Estate Podcast, Nathan Sosa and Matt Hamilton break down the complexities of Qualified Opportunity Zones (QOZs) and why this tax incentive can be powerful for real estate investors. Nathan and Matt walk through: - What Qualified Opportunity Zones and Qualified Opportunity Funds (QOFs) are designed to do - How investors can defer capital gains and potentially eliminate tax on long-term appreciation - Why QOZ investments must be structured through partnerships and not single-member LLCs - The 10-year hold requirement, step-up in basis, and how depreciation recapture can be avoided - Key differences between investing in raw land, new construction, and existing property improvements - The penalties for failing the 90% test and how to manage cash at the fund level - How upcoming tax law changes in 2026 and 2027 reshape the rules for future investments - Why state-level QOZ rules may differ from federal rules and what that means for deal structuring They also discuss real-world investor strategies, the marketing benefits syndicators can highlight when raising capital, and why working with a CPA who understands QOZ compliance is critical to avoid penalties, reporting issues, and missed tax savings. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

  32. 10

    09. Property Contributions in Partnerships: Avoiding Disguised Sales

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton dive into the tax and legal complexities of contributing property to a partnership and why the IRS’s disguised sale rules can turn a seemingly simple transaction into a taxable event. Nathan and Matt walk through: - How property contributions work under partnership tax rules - Why partnerships offer flexibility for moving assets in and out, most of the time - What qualifies as a disguised sale and why it’s “just a sale with extra steps” - Real-world examples where investors accidentally trigger taxable events - The impact of existing debt on contributed property and partner capital accounts - How built-in gain, basis preservation, and bonus depreciation limits come into play - Key pitfalls in 721 transactions and when to involve your CPA and attorney early They also cover why proactive planning and clear deal structuring are critical to avoid IRS scrutiny, unexpected tax bills, and unnecessary headaches. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  33. 9

    08. Your Next Strategic Tax Moves Amid Bonus Depreciation Changes

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton break down the latest wave of questions surrounding 100% bonus depreciation under the "Big Beautiful Bill", with a special focus on the critical January 19 cutoff date that’s caught many investors off guard. Nathan and Matt walk through: - Why 100% bonus depreciation is top of mind for real estate syndicators in 2025 - How the January 19 acquisition deadline creates a narrow window - What syndicators and developers need to know about acquisition vs. development timelines under the new rules - When a project is considered “acquired” and how the 10% construction threshold applies in self-construction scenarios - Whether component elections or Section 179 expensing offer viable workarounds for those who miss the cutoff They also discuss how proactive planning, clean accounting records, and collaboration with attorneys are more important than ever as investors navigate unclear regulations and wait for Treasury guidance. This episode is a must-listen for operators, fund managers, and advisors structuring deals in 2025. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  34. 8

    07. Preferred Returns in Real Estate Syndications: The Good, The Taxed, and The Risky

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton explain how preferred returns work in real estate syndications, how they're taxed, and the key details that often get overlooked in fund structuring. Nathan and Matt walk through: - What preferred returns are, how they’re typically structured, and why most syndications include them - Why PREF equity payments are usually not considered guaranteed payments and how that affects self-employment tax - How capital calls are becoming more common, especially in deals affected by rising interest rates and bridge loan maturities - The difference between accrued and non-accrued PREFs, and how that changes what investors are owed at liquidation - When preferred returns are treated as guaranteed and why that’s extremely rare The conversation also covers how poor deal structuring and vague operating agreements can put GPs at risk of getting paid last or not at all. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  35. 7

    06. PADS: How One Tax Move Saved a Client Almost $1M in Deductions

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton dive into one of the most overlooked, but highly impactful, real estate tax strategies: partial asset dispositions (PADs). Nathan and Matt walk through: - What a PAD actually is and how it prevents you from depreciating the same asset twice - Why failing to write off disposed components (like a roof or HVAC unit) is one of the most common missed deductions - How one client saved nearly $1 million in deductions by cleaning up depreciation schedules - The difference between proactive and retroactive PAD strategies and which one you should be doing - And more Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  36. 6

    05. What Syndicators Need to Know About the OBBB: Bonus Depreciation, 179 Expensing, and Tax Traps

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton break down the massive tax legislation signed on July 4th and what it means specifically for real estate syndicators. Nathan and Matt walk through: - How 100% bonus depreciation became permanent and what that means for deal structuring - The unfortunate “unlucky two weeks” in January 2025 and how they impact depreciation eligibility - Why Section 179 deductions got a boost and when syndicators might actually use them - How interest expense limitations are changing and the fading relevance of 163(j) elections - A new and intriguing provision: full expensing for qualified production property and how syndicators might creatively structure deals around it - What did not make it into the bill, including carried interest reforms and changes to SALT caps - Updates on Qualified Opportunity Zones (QOZs), including permanent extensions, rural incentives, and step-up timelines You’ll also hear how these changes may reshape fund strategy, planning for new developments, and even open new doors in industrial and manufacturing syndications as long as you follow the rules. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  37. 5

    04. Deficit Restoration Obligations: Strategic Tax Move or Major Risk for GPs?

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton dig into one of the most powerful and riskiest tools available to general partners: the Deficit Restoration Obligation (DRO). Nathan and Matt walk through: - What a Deficit Restoration Obligation actually is, and why it allows you to go negative in your capital account - When DROs show up in operating agreements and why they usually don’t - Why DROs are considered a “tool of last resort” in tax strategy - The difference between limited and unlimited DROs (and the consequences of both) You’ll also hear about real-world client experiences, handshake deals gone sideways, and why working closely with your CPA and attorney is non-negotiable when DROs are on the table. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  38. 4

    03. How to Structure Partnership Allocations the Right Way: Capital, Compliance, and Consequences

    In this episode of the Major League Real Estate Podcast, Nathan Sosa and Matt Hamilton break down one of the most misunderstood, yet critical, components of real estate syndication: capital accounts and how they relate to partnership allocations. Starting with the basics, Nathan and Matt break down: - What capital accounts are and how they track contributions, distributions, income, and losses - Why negative capital accounts matter, and how they impact your ability to claim losses - Section 704(b) of the Internal Revenue Code and its requirement that allocations have “substantial economic effect” - The myths and mistakes many GPs make when trying to shift losses without shifting true economic risk - And a lot more You’ll also hear why every operating agreement is really a dis-operating agreement, and what that means for structuring your deals from day one. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  39. 3

    02. Breaking Down Depreciation in Syndications: Allocation, Recapture, and Bonus Timing

    In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton take a technical dive into the mechanics of real estate depreciation and its role in tax strategy for syndications. Together, they unpack: - What depreciation is and why it matters in real estate investing - The difference between depreciable basis and land allocation - How depreciation schedules are determined (27.5 vs. 39 years) - The significance of “placed in service” and capitalization thresholds - How improvements, repairs, and settlement costs impact basis - Cost segregation studies: methodology, compliance, and benefits - The role of accelerated depreciation and bonus eligibility - Depreciation recapture: ordinary income vs. capital gains treatment - Why depreciation isn't a “tax loophole,” but a timing strategy - Strategic use of amortization, loan cost recovery, and tax planning windows Nathan and Matt also cover how the 2025 tax bill could impact bonus depreciation and what real estate investors need to know before year-end. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

  40. 2

    01. Understanding Real Estate Syndications: Tax, Structure & Strategy

    In this episode of the newly relaunched Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton take you through a full-cycle deep dive into real estate syndications, from the mechanics of deal structuring to the complex world of tax implications. Together, they break down: - What a real estate syndication actually is - Why it's such a popular vehicle for real estate investment - The tax advantages of syndications for both GPs and LPs - How partnerships differ from S corps and C corps - Roles and responsibilities of general partners (GPs) - How cash waterfalls and 80/20 profit splits work - Common pitfalls like phantom income and capital account surprises - Key tax documents: Form 1065, K-1s, operating agreements, and PPMs - Tax planning strategies for both limited and general partners Stay tuned, Nathan and Matt will be diving deeper into topics like depreciation allocations and 1065 filings in upcoming episodes. Request a free discovery meeting: https://go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: https://go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: https://go.therealestatecpa.com/mlreultimateguide The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

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ABOUT THIS SHOW

The Major League Real Estate Podcast is the show for operators and sponsors who compete at the highest level. We dive deep into the journeys, investing frameworks, and tax strategies of elite portfolio builders, all while spotlighting these playmakers who build and scale multi-million-dollar portfolios. Whether you're syndicating deals, managing large assets, or scaling partnerships, you’ll hear firsthand how top performers get it done. We explore every strategy related to acquisitions, operations, and exits and break down the best ways to optimize your taxes for each one. Tune in for real stories, sharp insights, and proven frameworks you can use right now.

HOSTED BY

Hall CPA

Produced by Major League Real Estate

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