Live Tax Q&A: 12 Real Tax Questions From Business Owners

What does the IRS actually care about? In June 2026 I sat down for an open Q&A with members of the mycpapro newsletter and answered real questions from real business owners and high earners. No hypotheticals. No "it depends" non-answers. Just the math, the rules, and the war stories. The questions we covered: → Can you really call your stay-at-home spouse a "real estate professional"? → Once you qualify as a real estate professional, do you stay qualified? → Does being a real estate professional cut your tax when you sell? → Is the short-term rental "loophole" everyone posts about actually real? → Short-term vs long-term rental — which should you even buy? → I make $400K on a W-2 — why do my business-owner friends pay nothing? → I got money back from my oil & gas well — is that recapture? → Are workforce-housing and equipment-rental strategies actually good for you? → I'm an LP in a stack of syndications — what do I do after the 5-year exit? → Can a passive investor (LP) take the oil & gas drilling deduction? → Where do all your passive losses actually go? → Same income as last year — so why did my tax bill explode? Each answer is its own chapter — jump to the one you came for, or watch the whole thing. Real questions, no fluff. ━━━━━━━━━━━━━━━━━━━━━━━━ 📩 WANT TO ASK YOUR OWN QUESTIONS LIVE? This Q&A is held for our community and only members of our newsletter get the invite. We send great content twice a week (real tax strategy for business owners, not fluff), plus the link to the next live Q&A. 👉 Join the newsletter: https://mycpapro.com/newsletter 📞 WANT TO TALK 1-ON-1? If you'd rather have me look at YOUR specific situation, book a free strategy call and we'll see if we're the right fit to work together. 👉 Book your free strategy call: https://mycpapro.com/yt ━━━━━━━━━━━━━━━━━━━━━━━━ ⏱ CHAPTERS 0:00 The big quotes + welcome 0:43 Can you call your spouse a "real estate professional"? 4:10 Do you stay a real estate pro once you qualify? 5:33 Does being a real estate pro cut the tax when you sell? 6:05 The short-term rental "loophole" — the truth 10:48 Short-term vs long-term — what every dollar must do 15:01 I make $400K on a W-2 — why do my friends pay nothing? 20:16 I got money back from my oil & gas well — is it recapture? 22:23 Workforce housing & "advanced" strategies — good for YOU? 26:30 Syndications as an LP — what to do after the exit 31:00 Oil & gas — LP vs GP and the drilling deduction 32:25 Passive losses & the 8582 "bucket" 34:28 Same income — why did my tax bill explode? (AMT) 35:40 Closing thoughts ━━━━━━━━━━━━━━━━━━━━━━━━ 🔔 Subscribe for more straight-answer tax videos for business owners and high earners. 🌐 Website: https://mycpapro.com 📅 Recorded: June 11, 2026 #TaxQA #SmallBusinessTaxes #BusinessOwner #HighIncome #TaxStrategy #CPA #TaxPlanning #RealEstateProfessional #ShortTermRental #Syndication #PassiveIncome #AMT ━━━━━━━━━━━━━━━━━━━━━━━━ Disclaimer: This video is for educational purposes only and is not tax, legal, or financial advice. Every situation is different — talk to a qualified professional about your specific facts before making any decisions.