Tax Smart Real Estate Investors Podcast

In this engaging episode, the hosts tackle real estate investors' burning tax questions. They explore intriguing topics like how short-term rental losses can impact income and the details of the QBI deduction. Listeners learn about the nuances of travel time and its role in material participation, alongside strategies for navigating home improvement records. They also discuss the critical 14-day rule and the complexities of bonus depreciation. It's a treasure trove of practical advice for optimizing tax benefits in real estate!

Chris Prefontaine, a real estate veteran with over 30 years in the industry and founder of Smart Real Estate Coach, shares invaluable insights on creative financing. He explains how to invest without banks, structure zero-interest seller financing deals, and navigate subject-to transactions. Chris discusses how the 2008 crisis reshaped his approach and highlights strategies like principal-only payments. Whether you're aiming for long-term rentals or avoiding traditional loans, his real-world examples offer a fresh perspective to thrive in any market cycle.

Dive deep into the world of tax scams targeting real estate investors. Learn why equipment leasing deals often miss the mark and how solar tax credits can be misrepresented. Discover the risks behind inflated art donation deductions and why they should raise red flags. Thomas and Ryan also discuss two high-risk strategies—discounted IRA rollovers and deferred sales trusts—that, while not outright scams, require extreme caution. Equip yourself with knowledge to protect your wealth from potential pitfalls!

In this engaging conversation, Jesse Vasquez, founder of AirVenture Academy, shares his journey from healthcare to becoming a midterm rental expert. He explains how he 2-3X’s rental income by securing long-term contracts with corporate clients, minimizing turnover issues typical of short-term rentals. Jesse discusses the advantages of midterm rentals, including fewer risks and more reliable tenants, and provides strategies for building partnerships with businesses like hospitals and relocation companies. Tune in to uncover the potential of this overlooked market!

In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with short-term rental investor Avery Carl, founder of the Short Term Shop and author of Smarter Short-Term Rentals, about how she grew one cabin purchase into a portfolio of over 250 units. Avery shares the blueprint for choosing the right vacation markets, designing systems for self-management, and avoiding costly pitfalls in today’s higher-rate environment. Tune in to learn: - Why buying where you’ve actually vacationed can give you a guest-focused edge. - How strategic pricing and technology keep your calendar booked—even off-season. - The real scoop on “mega-theming” and the simple design approach that still earns five-star reviews. - Tips for building a reliable local team when you’re investing from afar. - How Avery leverages the short-term rental tax strategy to keep more cash in her pocket. This episode will help you spot the right deals and scale sustainably. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Are You Ready for the 2025 Tax Changes? Click HERE to Access the FREE Tracker: go.therealestatecpa.com/4gDayj7 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli Connect with Avery: The Short Term Shop: theshorttermshop.com Avery Carl on Instagram: @theaverycarl and @theshorttermshop 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.

In this engaging discussion, Rob Abasolo, a short-term rental mogul and the creator of the Robuilt YouTube channel, shares his journey from copywriting to building a successful rental portfolio. He reveals why tiny homes and unique properties can command higher nightly rates. Rob emphasizes the impact of outdoor enhancements on revenue and offers practical tips on design and marketing. He also dives into tax strategies like bonus depreciation to maximize returns, plus his blueprint for scaling his upcoming projects!

Nathan Sosa, Head of National Tax at Hall CPA, brings his expertise to the table, discussing crucial 2025 tax updates for real estate investors. They dive into the uncertain future of bonus depreciation and the implications of possible tax rate changes. The conversation highlights the SALT deduction and its potential reforms, as well as survival strategies to navigate the shifting landscape. Sosa emphasizes the importance of preparation and tracking legislative developments to optimize tax savings, ensuring listeners stay informed and ready.

Dive into the essential world of depreciation in real estate investing. Discover how to maximize tax savings through strategies like cost segregation and bonus depreciation. Learn about the potential pitfalls of depreciation recapture and how to strategically plan to minimize its impact. Explore the lazy 1031 exchange, a clever way to defer taxes without the hassle of full exchanges. This engaging discussion equips investors with valuable insights to optimize their tax positions and boost their cash flow.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental investor Michael Chang to discuss how he went from Wall Street investment banker to building a 38-property short-term rental empire. Michael shares how he leveraged rental arbitrage, short-term rental tax strategies, and automation to achieve financial freedom. Tune in to learn: - How Michael transitioned from a high-pressure Wall Street career to full-time real estate investor. - The basics of rental arbitrage and why it’s an ideal starting point for new investors. - How Michael scaled his short-term rental business to 38 properties while optimizing for tax efficiency. - The key technology and AI tools that help him manage his portfolio remotely. - Strategies for reducing taxes and maximizing cash flow as a short-term rental investor. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Are You Ready for the 2025 Tax Changes? Click HERE to Access the FREE Tracker: go.therealestatecpa.com/4gDayj7 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli Connect with Michael: https://www.strlikethebest.com/ 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.

In our first monthly Q&A episode, Ryan and Thomas answer the most pressing tax questions from listeners. They tackle a variety of hot-button topics, including when flipping property income is considered “active” (and why that matters if you have a W-2), how partial asset dispositions really work, and whether or not a cost segregation study has to be performed in the first year. They discuss: - Flips & W-2 Incomes – Why these profits generally count as active, even if you’re not a real estate professional. - Partial Asset Dispositions – Deducting the cost of replaced components (like an old roof) to save on taxes. - Cost Seg Timing – Is it necessary to perform a cost segregation study in Year 1, or can you do it later? - Short-Term Rentals vs. REPS – Understanding when you do (and don’t) need real estate professional status. - Bonus Depreciation Updates – What investors need to know about the potential return of 100% bonus depreciation. Remember to submit your questions at contact@therealestatecpa.com or the Tax Smart Investors Facebook group. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Are You Ready for the 2025 Tax Changes? Click HERE to Access the FREE Tracker: go.therealestatecpa.com/4gDayj7 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.