Live Tax Q&A for Business Owners: 13 Real Questions, Answered (August 2026)

“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” non-answers where a real answer exists, just the math, the rules and the war stories. Watch the full session below, then jump to any individual answer.

Quick answer: This is the full August 2026 live tax Q&A for business owners and high earners. Use the links below to jump straight to your question — from S-Corp wages and the S-Corp profit threshold to short-term rental bans, QBI, cost segregation, the Roth 5-year rule and the new Trump accounts.

https://www.youtube.com/watch?v=dnXYa8YTcIY

Every question, with its own deep-dive

Each question below has its own full write-up. Click through for the detailed answer, the numbers and the FAQs.

1. My S-Corp made an extra $70K. What do I do first?
2. My city banned short-term rentals. Do I still get the tax benefits?
3. Should my rentals live inside an S-Corp? (Plus: is the K-1 active or passive?)
4. My LLC reimburses my home office. Can I still deduct property taxes on Schedule A?
5. I make $205K on a W-2 and I’m getting slaughtered every April. What can I do?
6. I’m turning my old house into a rental. Do I need an LLC?
7. One business makes money, one loses. Do I still get the QBI deduction?
8. At what profit does an S-Corp actually make sense?
9. Is cost segregation worth it? (Plus: is multifamily residential or commercial?)
10. How does the Roth 5-year rule work? (Plus: what if you have multiple Roths?)
11. What’s your honest take on the new Trump accounts?

Selling your rentals at 74: does “swap till you drop” erase the tax?

One question is answered only in the full video. A couple, both 74, own two long-term rentals and a short-term rental bought through a 1031 exchange with accelerated depreciation — and want out within two years without handing over a fortune in capital gains and depreciation “clawback.”

Laura’s first move is the same as always: decide what the exit is for. Preserve cash flow? Grow wealth into the next investment? Or fully get out? Each goal leads somewhere different — every dollar you invest can only give you appreciation, cash flow or a write-off, and a short-term rental is a season, not a long-term solution. Switching from active management to passive changes your options.

On the follow-up — does “swap till you drop” stop the clawback when the family inherits? It can: heirs generally receive a stepped-up basis at death, which can wipe out the deferred gain and the depreciation recapture. But it depends on who holds the deed, the state, whether there’s a trust and what the history of the property looks like. And moving into a 1031 property for two years to use the $500,000 home-sale exclusion buys less than people think: after serial exchanges there’s often little basis left, a property acquired in a 1031 must be owned for five years before the exclusion can apply, rental years can shrink the exclusion, and depreciation already taken is still taxed.

The short version of each answer

Want the one-line takeaways before you dive in? Here’s the gist of each question in this tax Q&A for business owners:

• Extra S-Corp profit: fix reasonable compensation first — the wage-vs-distribution gap is what draws IRS attention.
• Short-term rental ban: local law and tax law are separate; the benefits only help if you can legally operate.
• Rentals in an S-Corp: S-Corps are for active businesses; rentals are passive by law.
• Home office reimbursement: the reimbursed share can’t also go on Schedule A — prorate it.
• W-2 withholding: project the full year, then add withholding or pay a Q4 estimate.
• LLC for your old home: with one long-term rental, an LLC does almost nothing for your taxes.
• QBI with two businesses: everything nets together, and negative QBI carries forward.
• S-Corp profit threshold: roughly $40K–$70K of net profit, moved by your reasonable compensation.
• Cost segregation: amazing if you hold 5+ years; sell in 2–3 and recapture can erase the benefit.
• Roth 5-year rule: two clocks — open a Roth IRA today to start the one that matters most.
• Trump accounts: grade them by the exit; the flexibility at the end is the feature.

Why we run a monthly tax Q&A for business owners

Tax law isn’t stagnant — between new legislation, state-level changes and a flood of social-media “advice,” business owners and high earners are left guessing what actually applies to them. This monthly tax Q&A for business owners is our way of cutting through that noise and saying thank you to our community for reading our emails.

One lesson ran through this whole session: the more specific your question, the better your tax answer. Tax is calculation — bring the numbers and you get a strategy. It’s educational, not personalized advice, but it’s real answers to real questions, grounded in thousands of audit cases fought face-to-face with the IRS and the states.

Official IRS reference: IRS — Small Business and Self-Employed Tax Center

Key takeaways

• A full tax Q&A for business owners and high earners — 13 real August 2026 questions.
• Eleven questions have their own in-depth article; the rental-exit question is covered in the full video.
• Topics: S-Corps, short-term rentals, home office, withholding, LLCs, QBI, cost seg, Roth, Trump accounts.
• The more specific your question, the better your tax answer.
• The Q&A runs monthly; only newsletter members get the invite.

Live Tax Q&A FAQs

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Disclaimer: This article 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.