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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Your CPA says you make too much money. They say you work too many hours at your job. They say you need to be a real estate professional. All three of those statements are wrong.
In this episode, Michael sits down with Amanda Han and Matt MacFarland from Keystone CPA, two of the leading tax experts in the short-term rental space, to break down exactly how the STR tax loophole works, why most CPAs get it wrong, and how to protect yourself if the IRS ever comes knocking.
We break down:
- The three material participation tests that actually matter (500 hours, 100 hours with no one else having more, and more hours than everyone combined) and why married couples have a major advantage
- The grouping election that most CPAs miss entirely because it's a paragraph, not a form, and why this one oversight can destroy your audit defense when you scale to multiple properties
- What actually counts toward your hours (hint: it starts when you go under contract) and what doesn't count no matter how much time you spend on it
- A real IRS audit case study where the auditor automatically disallowed all losses because the properties were out of state, and how it ended with zero changes after proper documentation
- Why properties with lower land value create significantly larger tax benefits and which markets give you the best depreciation potential
- The three red flags that signal your CPA does not understand the STR loophole (if you hear any of these, it's time to find a new accountant)
- Best practices for documentation including RepsTracker, separate phone systems, dedicated email addresses, and why showing up as an "A plus student" changes everything in an audit
With bonus depreciation now permanent at 100%, this is the most meaningful window for high-income W2 earners to legally offset substantial income through short-term rental investing. But only if you do it right.
Check out Keystone CPA: https://strlikethebest.com/keystonecpa
Follow Amanda on Instagram: https://www.instagram.com/amanda_han_cpa
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod
Apply to work with Michael: https://strlikethebest.com/applypod
Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
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