Short-Term Rental Tax Planning
Does the short-term rental tax strategy actually fit you?
For physicians, attorneys, and other high-earning professionals who own or are considering a short-term rental. I help you find out whether the strategy applies before you rely on it, and set up the records to support it.
What's often called the "STR loophole"
Rental losses are usually treated as passive, which limits how they can be used. Under certain conditions, losses from a short-term rental may be treated differently and used against other income, such as wages or practice income.
Whether that applies depends on your facts, including how long guests typically stay, how involved you are in running the property, and how well that involvement is documented. It isn't automatic, and it isn't right for everyone.
This page is general information, not tax advice for your situation.
Sound familiar?
How I help
Already own the property? Start at step 3.
Ways to work together
STR planning session: $750
A 60-minute call plus a short written memo on whether the strategy appears to fit and what to document. The fee is credited toward your first month if you sign on.
Ongoing support
STR planning as part of Real Estate Investor Services, starting at $500/month.
Common questions
I already bought the property. Is it too late?
No. What matters most is how the property is operated and documented from here, so the sooner we look at it, the better. I review your situation and tell you what to track.
Do I need a property manager, or can I self-manage?
Not necessarily. A full-service manager can make the participation requirements harder to meet, depending on what the manager actually does. I look at the arrangement before you rely on the strategy.
Do you work with STR owners outside Florida, Virginia, and Montana?
Yes. I work with real estate investors anywhere in the US, remotely.
More questions →