393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned

Joey Linn went from covering NBA stars for Sports Illustrated to buying and remotely managing his first short-term rental in Michigan City, Indiana. The original motivation? A growing business had created a significant tax problem, and Joey saw short-term rental real estate as an opportunity to combine potential tax benefits with an appreciating, cash-flowing asset. But his first deal quickly became a real-world education in real estate investing. In this episode, Joey joins Thomas Castelli, CPA, and Nate Sosa to explain why he invested in the Midwest instead of Southern California, how he bought his first property without seeing it in person, and how he built a local team to manage the property remotely. Plus, Joey shares his journey from sports media to entrepreneurship, how AI is changing the sports-writing business, and what could be next for his real estate portfolio. Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nathan: go.therealestatecpa.com/question The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, 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.