Jul 3, 2026 · 32 min · 15 segments
For years, high-income professionals watched the STR tax loophole phase out and assumed it was gone for good. It's not. And the window to act is open right now. In this episode, I sit down with Ryan…
Michael ChangHost
Ryan BakeyGuest
We think that the SDR taxable, just to broadly define it, is you are able to buy a short-term rental, take bonus depreciation against that, and offset against that.

If you are working, you know, you're a high income professional, there are very, very few ways to reduce your taxes legally.

It's only been back for a year with the one big, beautiful bill, and it's been a big topic.


Yeah, for me, the real estate tax all started when I was working at my first accounting firm.



So I went to my boss and I was like, did I do this wrong? Am I going to get fired? He's like, no, it's because he's a real estate professional or it's because

So I started studying like the real estate tax code, particularly the section 469.

And in those rules, there's a little carve out for, well, hey, if you have a property, if you have a property where you're renting it out on average seven days or less, then it's not considered a rental property and it's not subject to those passive activity rules like a long-term rental or a multifamily building would be.

And in order to deduct that business loss against your active income, you have to materially participate, which means you have to spend a lot of working hours in the property, 100 hours and more than any other person, or you spend 500 hours total across all your properties.

It's just so funny because it's just this little couple of sentences, maybe, probably less than 300 characters where there's the exceptions to the rule.

But it's that little... paragraph that sparked this whole thing over the last, I would say, six, seven years with the short-term metal loophole.

And back in 2020 through 2023, people could put 10% down on a property, super low interest rate.

We think that the SDR taxable, just to broadly define it, is you are able to buy a short-term rental, take bonus depreciation against that, and offset against that.

If you are working, you know, you're a high income professional, there are very, very few ways to reduce your taxes legally.

It's only been back for a year with the one big, beautiful bill, and it's been a big topic.


Yeah, for me, the real estate tax all started when I was working at my first accounting firm.



So I went to my boss and I was like, did I do this wrong? Am I going to get fired? He's like, no, it's because he's a real estate professional or it's because

So I started studying like the real estate tax code, particularly the section 469.

And in those rules, there's a little carve out for, well, hey, if you have a property, if you have a property where you're renting it out on average seven days or less, then it's not considered a rental property and it's not subject to those passive activity rules like a long-term rental or a multifamily building would be.

And in order to deduct that business loss against your active income, you have to materially participate, which means you have to spend a lot of working hours in the property, 100 hours and more than any other person, or you spend 500 hours total across all your properties.

It's just so funny because it's just this little couple of sentences, maybe, probably less than 300 characters where there's the exceptions to the rule.

But it's that little... paragraph that sparked this whole thing over the last, I would say, six, seven years with the short-term metal loophole.

And back in 2020 through 2023, people could put 10% down on a property, super low interest rate.
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