Tax Strategy Blog for Business Owners

“What does the IRS actually care about? 13 real questions from real business owners and high earners.” This live tax Q&A for business owners and high earners is the full August 2026 session, where CPA and tax strategist Laura Dohanes answered 13 real questions from real owners and investors — no hypotheticals, no “it depends” […]

“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: […]

“If we move out of our home and rent it out, should we change the title to an LLC, or leave it in our names to deduct the expenses?” An LLC for rental property is the first thing people suggest when you move out and rent your old home. But there are two different questions […]

“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 […]