Tax Strategy Blog for Business Owners

“Is cost segregation something worth doing, or is it better to live only with regular depreciation?” Cost segregation recapture is the part of the pitch nobody leads with. The studies can be spectacular — but sell too soon and the write-off comes back at a higher rate than you’d have paid without it. Quick answer: […]

“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 […]