Episodes

  • 335. Syndication Legal 101: What Every First-Time Sponsor Must Know with Tilden Moschetti

    335. Syndication Legal 101: What Every First-Time Sponsor Must Know with Tilden Moschetti
    Jul 9 2025
    Before you syndicate your first deal, you need to get your legal foundation right. This week on the Tax Smart REI Podcast, we sit down with Tilden Moschetti, real estate attorney and experienced syndicator, to talk through the legal must-haves for your first capital raise. You'll learn: - When a deal becomes a syndication in the eyes of the SEC - The two-entity structure every sponsor should use - What PPMs, subscription agreements, and operating agreements actually do - Why you shouldn’t rely on capital raisers (and how to avoid SEC trouble) Whether you're raising $200K or $2M+, this episode is packed with real-world advice to help you syndicate legally and confidently. 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 Eckard Enterprises: eckardenterprises.com/taxsmartrei/ 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.
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    35 mins
  • 334. Grouping Elections: Why Your STR Doesn’t Belong with Your LTRs

    334. Grouping Elections: Why Your STR Doesn’t Belong with Your LTRs
    Jul 2 2025
    In this week’s episode of the Tax Smart REI Podcast, Thomas and Ryan answer real estate tax questions submitted by the community. From LLC structuring and grouping elections to retroactive cost segregation and solo 401(k) eligibility, this Q&A session covers some of the most common (and confusing) issues investors face midyear. Key topics covered: - Can I move my STR into an LLC if the deed and mortgage are in my name? - Why short-term rentals can’t be included in a Dash-9 grouping election - What counts as "placed in service" when a tenant isn’t paying rent - How to take 100% bonus depreciation in 2025 for a 2022 STR purchase 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 Eckard Enterprises: eckardenterprises.com/taxsmartrei/ 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.
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    19 mins
  • 333. The Senate’s version: Permanent 100% Bonus Depreciation

    333. The Senate’s version: Permanent 100% Bonus Depreciation
    Jun 25 2025
    In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, break down the Senate’s draft tax bill and what it could mean for real estate investors if it becomes law. Key topics covered: - 100% bonus depreciation made permanent: what this really means - Major changes to Qualified Opportunity Zones (QOZs) - Updates to Section 179 and interest expensing rules - The fate of the SALT cap and why it’s still a moving target - Expanded QSBS exclusion and its impact on startup investors - The Senate’s fix to Excess Business Loss (EBL) carryovers - Why QBI stays at 20% and who gets left out of the benefit Plus, Thomas and Ryan take questions from the Tax Smart community on short-term rentals without guest stays, the risks of self-preparing complex tax returns, and what happens when you sell a property at a loss. 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 Eckard Enterprises: https://eckardenterprises.com/taxsmartrei/ 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.
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    30 mins
  • 332. Can AI Replace Your Tax Advisor?

    332. Can AI Replace Your Tax Advisor?
    Jun 18 2025
    In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, put ChatGPT to the test to answer a question that’s on the minds of many real estate investors: Can AI actually replace your tax advisor? Key topics covered: - Where AI like ChatGPT performs well and where it fails - Real-time testing of ChatGPT on short-term rental strategies - Common AI mistakes on REPS, depreciation, and passive loss rules - A new listener question ChatGPT got both right and wrong - Why nuanced tax strategy still requires a real human advisor - How IRS regulations trip up AI systems - Real examples where relying on ChatGPT could lead to audit risk Plus, Thomas shares a fresh, real-world test he ran through ChatGPT just hours after recording and breaks down exactly where it gave conflicting answers. If you’re using AI to guide your tax decisions, this is an episode you don’t want to miss. 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.
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    31 mins
  • 331. The Overlooked Tax Move that Could Save You Tens of Thousands

    331. The Overlooked Tax Move that Could Save You Tens of Thousands
    Jun 11 2025
    In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, dive deep into Partial Asset Dispositions (PADs), a powerful but often overlooked tax strategy that can unlock substantial savings for real estate investors during renovations. Key topics covered: - What a partial asset disposition (PAD) is and how it works - When and how to claim a PAD on your tax return - Using cost segregation studies to support PAD calculations - Real-life case studies, including one client who saved over $2 million - When PAD losses are passive vs. non-passive - Why traditional CPAs rarely take advantage of this strategy - How to spot missed PAD opportunities in your depreciation schedule Plus, Thomas and Ryan explain which types of renovations typically qualify and how to make sure your CPA isn’t leaving valuable deductions on the table. 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.
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    19 mins
  • 330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore

    330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore
    Jun 4 2025
    In this episode of the Tax Smart REI Podcast, Thomas, Justin, and Ryan break down the most common (and costly) mistakes we see from other CPAs and the massive tax savings real estate investors are missing because of them. Tune in to learn: - Why electing out of bonus depreciation without knowing it can cost you tens of thousands - How improperly classifying repairs vs. improvements could trigger an audit or shrink your deductions - The overlooked grouping strategy that saved one client $150K+ in a single year - What really happens when CPAs misuse the Augusta Rule (and how to do it right) - How a "medical tax specialist" cost a client over $100K in phantom tax savings—and exposed them to penalties If you’re working with a CPA who doesn’t specialize in real estate, this episode might just save you from years of missed opportunities or worse, an audit. 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 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Wealth & Wisdom Event: https://www.dklawmd.com/events-calendar/wealth-and-wisdom-2025 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.
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    43 mins
  • 329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA

    329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA
    May 28 2025
    In this episode of the Tax Smart REI Podcast, Thomas, Troy, and Ryan unpack real IRS audit case studies involving real estate investors and break down exactly what happened, how they responded, and how they won. Tune in to learn: - What triggers IRS audits for short-term rentals and REPS (and how to avoid them) - The one thing most CPAs get wrong when representing clients in an audit - How a $209K tax bill was reduced to $296—with documentation and strategy - Why being “audit-ready” matters more than ever in the post-TCJA world - What to do (and not do) the moment you receive that dreaded IRS letter If you want to understand what an audit really looks like and how to protect yourself before one ever happens, this episode is a must-listen. 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 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.
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    44 mins
  • 328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST

    328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST
    May 21 2025
    In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down what real estate investors need to know about the draft of the 2025 tax bill, dubbed the “One Big, Beautiful Bill”, including what’s in it, what might change, and how to prepare for the opportunities it presents. Key topics covered: - The likely return of 100% bonus depreciation (and who qualifies) - SALT cap drama: why it could derail the bill - Changes to Qualified Opportunity Zones and what they mean for investors - Section 179 expensing increases for short-term rentals and asset-heavy businesses - QBI deduction bumps and simplified rules for service-based businesses - Full expensing for industrial facilities (and how it could spark a manufacturing boom) - “No tax on tips, overtime, or Social Security” — what made it in and what didn’t Plus, we cover what provisions are being made permanent, what’s being rolled back, and why now is the time to align with a tax advisor who knows how to play offense with the tax code. 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 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.
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    37 mins