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.
349. How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting
Tax Smart Real Estate Investors Podcast
36 minutes 43 seconds
1 month ago
349. How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting
In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Annette Grant and Sarah Karakaian, co-founders of Thanks for Visiting, to reveal what it really takes to run a profitable short-term rental business in today’s market.
Annette and Sarah have coached thousands of hosts on how to build scalable, hospitality-driven operations that actually make money. Together, they unpack the truth behind STR success, from pricing and KPIs to bookkeeping and mindset, and why short-term rentals are not the “passive income” opportunity many think they are.
You’ll learn:
- The #1 reason most hosts leave money on the table (and how to fix it)
- The five KPIs every short-term rental owner should track
- Why running a short-term rental is running a business, not just owning a property
- How clean bookkeeping and P&Ls protect you in an audit (and keep profits real)
- The right mindset for long-term success and how to balance cash flow, tax savings, and lifestyle goals
Whether you’re managing your first Airbnb or scaling a growing STR portfolio, this episode is packed with real-world advice on how to stop letting emotion drive decisions and start running your short-term rentals like a professional business.
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 Thanks for Visiting: https://thanksforvisiting.com/
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.
