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Results (3,433+)
Briley Roe Selling 4 properties in 1 year tax man wants 54k
14 November 2025 | 20 replies
What write offs/loopholes does anyone know of to help me in this situation. 1031 exchange is out of the question.
Adam Wachter Tax implications of using one unit in a multifamily property as a STR
17 November 2025 | 10 replies
So if only one of the four units is being rented out short-term and the other three are long-term, the overall average guest stay for the building would still exceed seven days—meaning it likely wouldn’t qualify as a short-term rental activity for the STR loophole.
William Thompson The Biggest Tax Mistake I See Real Estate Investors Make (and It’s Totally Avoidable)
19 November 2025 | 3 replies
*A few small habits — separate accounts, clean books, and talking to your CPA before year-end — can make a massive difference.Taxes aren’t about loopholes or tricks.They’re about getting organized early and using the rules the way they were written.Curious — when do you usually meet with your CPA?
Jorge D. how to offset capital gains from income investment?
14 November 2025 | 15 replies
If you sell the crypto in 2025 and then buy the STR AND meet all of the requirements of the STR loophole in 2026, you won't be able to offset 2025's gains.Id connect with a cpa to go through various scenarios so you understand the tax side.
AJ Wong ⚠️ The Clock Is Ticking: Use the STR Loophole Before 2025 Runs Out
15 October 2025 | 13 replies
Quote from @Collin Hays: Number one, there is no "loophole."
AJ Wong ✅ STR Tax Loophole Passed & other real estate investor tax provisions
15 October 2025 | 24 replies
Not a loophole it is tax law.
William Thompson Before You File: The Smart Investor’s Guide to Short-Term Rental Tax Breaks in 2025
28 October 2025 | 11 replies
That post does a killer job breaking down the STR Loophole!
Michael Carbonare 50 Year Mortgage: Terrible For Homeowners, Great For Lenders
14 November 2025 | 46 replies
After 15 years you could still owe $470K on a 50-year loan compared to $359K on a 30-year.What this really is:  a loophole for lenders/investors to lock you into decades of high interest. 
Joshua Koeppendoerfer New investor learning the ropes
13 November 2025 | 18 replies
Understand REPS, STR loophole, and Active participation to benefit from RE tax savings.Also, learn about the 1031 Exchange.
Diana Mulvihill STR Tax Classification Help - Primary Residence in Year One
29 October 2025 | 18 replies
I run the STR under an LLC, and my plan was to treat it as a business using what’s often called the “short-term rental loophole.”