Episode 508: Strategic Tax Planning for Real Estate Investors with Thomas Castelli

May 21, 2025

29:21

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On this week’s episode, I sit down with Thomas Castelli, real estate-focused CPA and partner at Hall CPA, to dive deep into real, practical tax strategies that can save investors thousands. If you’ve ever wondered whether your CPA is leaving money on the table, this episode will confirm your suspicion and give you the tools to fix it.

Thomas shares eye-opening stories of tax returns gone wrong, the truth behind cost segregation and depreciation, and how strategic planning done proactively can unlock massive wealth preservation.

Whether you’re a seasoned investor or just closing your first deal, these are the systems, mistakes, and mindset shifts that separate the average from the elite.

Key Talking Points of the Episode

00:00 Introduction

02:41 From accounting student to real estate investor to real estate CPA

04:02 Why generalist CPAs often cost investors money 05:14 The myth of “you can’t take more than $25K in losses”—and how pros work around it

06:10 How depreciation offsets income and reduces your effective tax rate 07:17 The $50K case study: a CPA missed cost segregation, costing a client dearly 08:18 Advisory vs. compliance: why strategy beats paperwork 10:02 Common mistakes: missed depreciation, unreported insurance, and more 12:02 Opting out of bonus depreciation—when it helps and when it hurts

14:47 What is cost segregation? 18:12 Which items can be carved out in a cost seg: carpets, appliances, sheds & more 19:15 Should you run a cost seg if you plan to sell in 2 years?

21:36 Get in touch with Thomas and his team

22:26 Why real estate is the best long-term tax strategy in America 24:30 Tax planning isn’t a luxury—it’s your responsibility

Quotables

“Most CPAs are generalists. If they don’t live in real estate, they don’t know what to look for.”

“Your tax return is a report card for what already happened. If you want to influence it, you have to act now.”

“This is like surgery. You don’t do it yourself. You call the right specialist.”

Links

Tax Smart Real Estate Investors Podcast

https://www.therealestatecpa.com/podcasts/

Hall CPA

http://smartrealestatecoach.com/hallcpa

QLS Live