10/28/2026
Everybody wants the short-term rental loophole.
But there are a few things that can really trip you up if you don’t follow the rules.
I asked for video suggestions recently and somebody said, "give us the common pitfalls with short-term rentals."
Great question. Because the pitch on social media sounds amazing, right?
Buy a beach condo. Rent it out a few nights at a time. Do a cost segregation study. Wipe out your W-2 income.
Here’s how the math works.
Say you buy a $1,000,000 condo. It rents for $60K a year. After interest, HOA dues, and every other expense, you net about $20K.
Regular depreciation runs about $25K a year. Small paper loss.
Now add a cost seg study. An engineering firm walks the property and pulls out the flooring, light fixtures, appliances. Stuff that qualifies for bonus depreciation. Typically 20 to 30% of the property. Call it 25%.
That’s $250,000 of deductions in year one.
Your $20K profit just became a $230,000 loss on paper.
That’s what everybody’s talking about when they say the short-term rental loophole.
But there are two traps.
Trap #1: Material participation.
Renting 7 days or less on average gets you out of the passive bucket. That’s only half the test. You also have to materially participate in the activity. Personally. With proof.
Got a property manager handling everything? That gets hard fast.
Miss this and you’ve done nothing. The loss only offsets passive income. Your W-2 stays untouched.
Trap #2: Depreciation recapture.
Take that $250K deduction and your basis in the condo drops to $750K.
Sell it a couple years later for $900K. Less than you paid for it.
You still have a $150,000 gain.
How? You already enjoyed $250K of that cost as deductions. When you sell, it comes right back as income. And properties normally appreciate.
I’ll leave you with this.
If someone is pushing you to do a cost seg on a short-term rental and they haven’t asked how you’re documenting your average stay or your hours, be careful. That’s an aggressive position. Tough to defend in an audit.
The best real estate advisors I know won’t even take you on as a client without contemporaneous records. Logs kept as you go, all year long.
Short-term rentals can be a great play. Go in with your eyes open.
Document everything. Know your exit before you buy.