Sunny Patel

Consider a contractor reviewing a $100,000 equipment quote in October. The dealer highlights a potential tax deduction. The machine could help handle bigger projects, but those jobs are not signed yet, and several customers still owe money.

I've been paying our family health premiums through the business for six years. My CPA never said anything, so I assumed it was handled. It wasn't. The premiums ran through the S corporation as a business expense, but they never appeared on his W-2. Under the rules, that means the plan wasn't established by the business, and the personal deduction is gone.

I sold a rental property last year and made $180K on the sale. Then tax season came and I found out I owed $80K, most of it from depreciation recapture. My CPA never mentioned it until the return was already done.