How One STR Property Can Save $370K in Taxes (And Why We're Never Selling It) episode artwork

EPISODE · Aug 7, 2026 · 23 MIN

How One STR Property Can Save $370K in Taxes (And Why We're Never Selling It)

from STR Like The Best · host Michael Chang

Most investors think the endgame is to buy, hold, and eventually sell. But selling might be the most expensive decision you ever make.In this episode, Michael and Liz share a real-time breakdown of their newest short-term rental, a $2.4M Tennessee property launched July 1st, covering the actual cash flow numbers, the tax strategy behind it, and why they plan to hold it for generations.This is one of the most transparent, numbers-first episodes we've done. No hypotheticals. Just the real performance data, the cost segregation results, and the Section 1014 strategy that changes how you think about real estate as a long-term wealth tool, all recorded while managing the property from 12 time zones away in Taiwan.We break down:How the property hit $30K in revenue and 82% occupancy in its very first month, before professional photos were even liveWhy the cost segregation study is projecting $800K to $1M+ in protected taxable income from this single property, and how an on-site engineering study could push that number even higherThe Section 1014 strategy that lets you pass real estate to your kids completely free of capital gains tax and depreciation recaptureHow Michael and Liz manage 12 properties remotely in about an hour a day each, whether they're in New York or 12 time zones awayWhy they only use 30-year fixed-rate debt, never underwrite a refinance, and model a conservative 3% annual appreciation when analyzing a dealHow $370K in projected tax savings effectively returns more than half their original cash investment in year oneThe bottom line: The real power of STR investing isn't just the cash flow. It's what happens when you stack cost segregation, bonus depreciation, and Section 1014, and hold the asset long enough to change your family's financial future.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

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Most investors think the endgame is to buy, hold, and eventually sell. But selling might be the most expensive decision you ever make. In this episode, Michael and Liz share a real-time breakdown of their newest short-term rental, a $2.4M Tennessee property launched July 1st, covering the actual cash flow numbers, the tax strategy behind it, and why they plan to hold it for generations. This is one of the most transparent, numbers-first episodes we've done. No hypotheticals. Just the real per...

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How One STR Property Can Save $370K in Taxes (And Why We're Never Selling It)

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