Episodes

  • 360. Why Short-Term Rentals Are Still the #1 Tax Strategy for 2026 ( + New Tax Court Case)

    360. Why Short-Term Rentals Are Still the #1 Tax Strategy for 2026 ( + New Tax Court Case)
    Jan 5 2026
    In this episode of the Tax Smart REI Podcast, Thomas Castelli discusses the #1 tax strategy for 2026, plus a new tax court case involving the real estate professional status (REPS) and a short-term rental. If you're a high-income earner, this is for you. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX 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.
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    27 mins
  • 2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)

    2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)
    Dec 31 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa discuss the top 2026 tax strategies and what moves you can still make for 2025 after the year ends. If you're looking to hit the ground running in 2026 and capture any final 2025 moves - this is for you. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Get the Year-End Tax Checklist: go.therealestatecpa.com/4pj63id 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.
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    24 mins
  • 358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A

    358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A
    Dec 16 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa discuss last minute 2025 tax strategies and questions we receive from Tax Smart Investors. If you're trying to figure out what you can do before the clock strikes midnight in two weeks, this episode is for you. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Get the Year-End Tax Checklist: go.therealestatecpa.com/4pj63id 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.
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    29 mins
  • 357. Cost Segregation Done Right - How In-Person Engineering Maximizes ROI with Edward Griffith

    357. Cost Segregation Done Right - How In-Person Engineering Maximizes ROI with Edward Griffith
    Dec 8 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa sit down with cost segregation expert Edward Griffith to break down what investors really need to know about cost segs—why engineering-driven, in-person studies deliver superior results, and how relying on cheap or software-only reports can quietly cost investors tens of thousands and increase audit risk. You’ll learn: - What a cost segregation study actually is, why it matters, and which properties generate the biggest ROI - Why in-person, engineering-driven cost segregation consistently produces higher ROI and stronger IRS defensibility than software-only reports - How the timing of a study (including pre- and post-renovation) affects your tax strategy and bonus depreciation opportunities - What the full cost seg process looks like from start to finish, and how to ensure deductions actually show up on your tax return To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Get the Year-End Tax Checklist: go.therealestatecpa.com/4pj63id 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.
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    25 mins
  • 356. The Missing Step in Cost Segregation Putting Real Estate Investors at Audit Risk

    356. The Missing Step in Cost Segregation Putting Real Estate Investors at Audit Risk
    Dec 3 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli, Nathan Sosa, and Justin Shore unpack what’s really happening inside today’s IRS cost segregation audits - why certain studies get challenged, the patterns auditors are catching, and the hidden risks most investors never hear about. You’ll learn: - The #1 issue auditors are flagging in cost segregation studies (and why software reports get hit hardest) - Why missing link that can tank a study’s defensibility and lower your depreciation results - How recent updates and language in the IRS Cost Segregation Audit Technique Guide signal a shift in scrutiny - What the AmeriSouth case tells us about “quality” studies—and how to avoid repeating the same mistake - Whether software-driven providers might be becoming more conservative and what that means for your ROI Perfect if you want to understand how to protect your deductions, avoid audit headaches, and ensure your next cost segregation study is actually audit-ready. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Get the Year-End Tax Checklist: go.therealestatecpa.com/4pj63id 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.
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    24 mins
  • 355. Tax Strategies No One’s Talking About (That Save Real Estate Investors a Fortune)

    355. Tax Strategies No One’s Talking About (That Save Real Estate Investors a Fortune)
    Nov 26 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down under-the-radar tax strategies real estate investors and high earners can use to cut their tax bills—plus the mistakes that quietly cost people thousands. You’ll learn: - How land banking works, who it fits best, and why it can be a powerful long-term tax play - The advanced “1031” strategies including reverse and improvement exchanges to defer taxes while upgrading properties - Niche but huge deductions like solar (only if you own the panels) and casualty losses - Two common pitfalls: accidentally triggering the 3.8% NIIT and missing the §469 grouping election that can trap losses. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Connect with Engineered Tax Services: portal.engineeredtaxservices.com/cost-seg…regation Get the Year-End Tax Checklist: go.therealestatecpa.com/4pj63id 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.
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    35 mins
  • 354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)

    354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)
    Nov 19 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa field real questions from the Tax Smart Investors Facebook group, their online community, and recent client conversations to tackle the most common and most confusing year-end tax issues real estate investors are facing. You’ll learn: - Why you must take depreciation on your rental properties - When you’re stuck with 40% vs 100% bonus depreciation - How short-term rental hours do (and don’t) count toward real estate professional status - When using a property manager or a seller staying in the property after closing can blow up your short-term rental strategy - The tests you need to meet if you want syndication losses to be non-passive - Why condos still need a land allocation for depreciation even if you “don’t own the dirt” Practical year-end action items: time logs, charitable bunching, retirement contributions, and how to use the free Year-End Tax Checklist without panic-buying a bad deal for a one-year tax win Whether you’re trying to squeeze in a year-end short-term rental, line up a cost seg study, or simply avoid costly mistakes on your 2025 return, this episode will help you zoom out, think long term, and decide which moves are truly worth making before December 31st — and which ones can wait. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Connect with Engineered Tax Services: https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation Get the Year-End Tax Checklist: https://go.therealestatecpa.com/4pj63id 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.
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    35 mins
  • 353. The Mega Backdoor Roth 401(k): What High-Income Earners Should Know with Alex Savage

    353. The Mega Backdoor Roth 401(k): What High-Income Earners Should Know with Alex Savage
    Nov 12 2025
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa, Head of the National Tax Department at Hall CPA, sit down with Alex Savage, CPA, CFP, to unpack the Mega Backdoor Roth 401(k), one of the most powerful yet underutilized tax strategies for high-income earners. They break down how the strategy works, who qualifies, and why it can be a game-changer for those looking to build long-term, tax-free retirement wealth, all while balancing real estate investing and other income streams. From contribution limits and in-plan conversions to control group rules and timing, this episode covers everything you need to know to decide whether this advanced strategy fits your situation. You’ll learn: - What makes the “Mega” Backdoor Roth 401(k) different from a traditional or standard Roth IRA - How high-income W-2 earners and solopreneurs can contribute up to $70,000+ in after-tax dollars - Why this strategy can help you manage future tax rates, Social Security taxation, and estate planning - The key testing and timing rules to avoid IRS pitfalls - When a Mega Backdoor Roth makes sense and when real estate might be the better play Whether you’re a tech executive, business owner, or high-earning real estate investor, this episode gives you the clarity to determine if the Mega Backdoor Roth 401(k) belongs in your financial toolkit and how to use it strategically alongside your real estate portfolio. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Connect with Engineered Tax Services: https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation Get the Solar White Paper: www.therealestatecpa.com/solar-white-paper/ 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.
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    28 mins