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 Realm,” 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.
All content for Tax Smart Real Estate Investors Podcast is the property of Hall CPA and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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 Realm,” 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.
354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)
Tax Smart Real Estate Investors Podcast
34 minutes 44 seconds
1 week ago
354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)
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.
Tax Smart Real Estate Investors Podcast
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 Realm,” 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.
