Tax Smart Real Estate Investors Podcast
Hall CPA
The Tax Smart Real Estate Investors Podcast is a show that focuses on tax, accounting, and finance tips for real estate investors and business owners. We bring on guests to talk through complex topics and we break it down into bite-sized chunks of knowledge for our listeners.
Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode.
Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
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
Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode.
Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
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
Episodes
Mentioned books
Feb 26, 2026 • 27min
MLRE: The Syndication Mistakes I'd Never Make Again (An Investor Deep Dive)
Thomas Castelli, Partner at Hall CPA and former syndicator and multifamily investor, shares firsthand tales from closing deals, weathering hurricane due diligence, and exiting during COVID. He talks about capital raising mistakes, the importance of investor relationships, underwriting and submarket analysis, insurance risks in hurricane zones, and how a failed fund shaped his approach to syndications.
Feb 24, 2026 • 27min
366. AI vs. The IRS: What Every Investor Must Learn from This Tax Court Case
A Tax Court case unravels after DIY returns trigger an IRS reconstruction from bank deposits and 1099s. The defense leaned on AI-generated, fabricated case citations that destroyed credibility. Missing closing statements lead to disallowed depreciation on rentals. The conversation highlights why precise bookkeeping, solid documentation, and qualified tax help matter for real estate investors.
Feb 17, 2026 • 47min
365. Can You Really Write Off a Private Jet? What Actually Works with Preston Holland
Preston Holland, founder of Prestige Aircraft Finance who advises high-net-worth clients on aircraft financing and structuring. He breaks down four ways to fly private. They discuss when buying a jet makes financial sense. They cover bonus depreciation, the 51% business-use rule, IRS scrutiny and required documentation.
Feb 9, 2026 • 25min
364. The Tax Questions High-Income Real Estate Investors Are Asking in 2026
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa answer the most pressing questions from real estate investors and high-income earners in 2026.
If you're investing in real estate, you may very well have these same questions.
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.
6 snips
Feb 3, 2026 • 34min
363. Tax Filing Mistakes That Cost Real Estate Investors Thousands
A deep dive into costly tax filing pitfalls that trip up real estate investors. They explain why short-term rentals often belong on Schedule E, not Schedule C, and what counts as substantial services. Learn when extensions help and why estimated payments still matter. Hear about dangerous elections like opting out of bonus depreciation and common LLC and filing misclassifications.
33 snips
Jan 27, 2026 • 30min
362. The Quiet Strategies High-Income Investors Use Instead of REPS or STRs
A crash course on why rental real estate gets special tax treatment and how depreciation can create paper losses while properties still cash flow. Practical tactics for using refinancing, BRRR and tax-free cash-outs to fund growth. Strategies to defer gains with 1031s, use DSTs and 721 swaps for passive exits, and rely on step-up in basis as the long-term endgame.
Jan 18, 2026 • 41min
361. You Don’t Need 10 Units: What One STR Can Actually Do for Your Taxes with Jason Smith
In this discussion, Jason Smith, a former high-income W-2 earner turned short-term rental (STR) owner, shares his journey into the STR world. He reveals how he saved over $30k in taxes through strategic depreciation and seller financing. Jason explains his personal management style, earning Superhost status with exceptional guest experiences, and the secrets of his time-tracking for material participation. He also offers insights on the local market outlook and shares valuable advice for prospective STR investors.
Jan 5, 2026 • 27min
360. Why Short-Term Rentals Are Still the #1 Tax Strategy for 2026 ( + New Tax Court Case)
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.
21 snips
Dec 30, 2025 • 24min
359. 2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)
Dive into essential tax strategies for 2026 and what you can still do for 2025. Discover the perks of cost segregation and learn how short-term rentals can benefit high W-2 earners. Explore the differences between traditional and 'lazy' 1031 exchanges, along with updates on Qualified Opportunity Zones. Plus, find out about the new charitable deduction rules and the impending solar credit sunset. Plan ahead for 2026 with insights that can give you an advantage in real estate investing!
Dec 16, 2025 • 29min
358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A
Discover crucial 2025 tax strategies before it's too late! Learn about the impact of the One Big Beautiful Bill, including bonus depreciation and SALT changes. Explore short-term rental qualification rules and the importance of keeping participation logs to avoid audits. Find out how to tackle reporting obligations like W-9s and 1099s, and understand the nuances of married filing separate in relation to REP status. Plus, get pro tips on year-end planning and the potential for Opportunity Zone deferrals!
