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  • 363. Tax Filing Mistakes That Cost Real Estate Investors Thousands

    363. Tax Filing Mistakes That Cost Real Estate Investors Thousands
    2026/02/03
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the most common - and most expensive - real estate tax filing mistakes investors make, and why many of them don’t show up until tax season, when it’s already too late to fix them. This episode is for high-income W-2 earners, business owners, and real estate investors who want to ensure they file correctly, protect their tax strategy, and avoid preventable leaks. If you want to understand the filing side of real estate taxes and avoid the errors that cost investors the most, this episode is required listening. 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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    34 分
  • 362. The Quiet Strategies High-Income Investors Use Instead of REPS or STRs

    362. The Quiet Strategies High-Income Investors Use Instead of REPS or STRs
    2026/01/27
    In this episode of the Tax Smart REI Podcast, Thomas Castelli breaks down how high-income earners can legally build tax-advantaged, tax-free income through real estate - even without REPS or short-term rentals. You’ll get a practical crash course on how the U.S. tax system actually works, why real estate is treated so favorably by the IRS, and how savvy investors use depreciation, refinancing, and smart exit strategies to increase cash flow while lowering their effective tax rate. This episode is for high-income W-2 earners, business owners, and real estate investors who want to zoom out, understand the bigger picture, and stop chasing one-off tax hacks. If you’re looking to build long-term, tax-efficient wealth through real estate -- this is your roadmap. 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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    30 分
  • 361. You Don’t Need 10 Units: What One STR Can Actually Do for Your Taxes with Jason Smith

    361. You Don’t Need 10 Units: What One STR Can Actually Do for Your Taxes with Jason Smith
    2026/01/18
    In this episode of the Tax Smart REI Podcast, Thomas Castelli and Alex Savage are joined by Hall CPA client, Jason Smith, to discuss a real first-year short-term rental case study, including how Jason, a high-income W-2 earner, legally generated $30k+ in tax savings through material participation, strategic depreciation planning, and proper structuring. This episode is for high-income earners who want to understand what it actually takes to use short-term rentals as a proactive tax strategy—without cutting corners or risking compliance. If you're on the fence about jumping into the STR game, this one 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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    41 分
  • 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)
    2026/01/05
    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 分
  • 359. 2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)

    359. 2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)
    2025/12/30
    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 分
  • 358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A

    358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A
    2025/12/16
    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 分
  • 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
    2025/12/08
    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 分
  • 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
    2025/12/03
    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 分