Tax Strategy Blog for Business Owners

“What tax advantages are available for a residential property that has a short-term rental entitlement, in a city that doesn’t have many legally operating STRs?” A short-term rental ban in your city doesn’t rewrite the federal tax code — but it can take the strategy off the table anyway. That’s the confusion behind this question […]

Qualifying your short-term rental was step one. Most owners stop there, take the deduction the default way, and leave the biggest part of it sitting on a schedule that runs for decades. A short-term rental cost segregation study is the second decision, and it controls how big the deduction gets. The study breaks the property […]

“If I don’t have material participation, is there any benefit of acquiring a short-term rental (as opposed to a long-term rental) from a tax perspective?” Short-term vs long-term rental is the question every real estate investor agonizes over — and it’s the wrong question. Reframe it with the rule Laura uses for every investment decision, […]

“If I buy a short-term rental, I can just write off the losses against my W-2, right?” The short-term rental loophole is all over social media — buy a short-term rental, write the losses off against your W-2. It can work. But social media shows you the best case, not the two hurdles almost everyone […]

“My spouse doesn’t really work — can’t we just call her a real estate professional and wipe out my W-2 with the rental losses?” Calling a stay-at-home spouse a real estate professional to erase a W-2 with rental losses is one of the most repeated moves in real estate tax circles — and one of […]

“What does the IRS actually care about? Real questions from real business owners and high earners.” This live tax Q&A for business owners and high earners is the full June 2026 session, where CPA Laura Dohanes answered real questions from real owners and investors — no hypotheticals, no “it depends” non-answers, just the math, the […]

“I own 12 rental units, and I still pay a fortune in taxes. If I just put them in an LLC, that fixes it, right?” Putting rentals in an LLC is the move most landlords reach for first — but the honest answer surprises them: the LLC wrapper, on its own, doesn’t drop your tax […]