Tax Strategy Blog for Business Owners

“With an S-Corp, minus reasonable compensation, the income is passive, correct? So real estate depreciation could reduce it?” Using an S-Corp for rental property sounds smart when a brother, a friend or half the internet says it’s the best structure. But S-Corps are built for active businesses — and rental real estate is passive by […]

“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 […]

If you own a rental, there is a good chance you are sitting on a deduction you never claimed. Not a gray-area deduction. Depreciation you were entitled to, and never took. Missed depreciation on rental property can be caught up in a single adjustment on this year's return. The tax code calls the mechanism a […]

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 […]

“I’m an LP in a lot of syndications generating K-1 depreciation. After a 5-year exit, do I 1031 into another deal — or what’s the best strategy?” A syndication exit strategy is the thing most passive real estate investors never think about until it’s too late. Getting into a deal is easy; the question is […]

“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 […]

“How do I know if I should get a cost seg study done? I have two long-term properties valued at $130K and $211K.” Cost segregation is one of the most talked-about real-estate strategies of the decade — but only for the right properties. Before you pay for a study, you have to do the math. […]