The exact months to file, elect, place assets in service, and restructure — so every legal deduction actually lands on your return.
March 15 is the hard deadline to elect S-corp for the current tax year. File Form 2553 with proper shareholder consent and reasonable-comp planning.
Must be established (and adopted in writing) by 12/31 to allow employee deferrals for that year — set it up before year-end, then contribute up to filing deadline.
Send to contractors and file with IRS by 1/31 (NEC) and 2/28/paper or 3/31/e-file (MISC). Missing filings kill business expense deductions on audit.
Due 3/15. K-1s must be issued to owners before they can file personal returns. Extend with Form 7004 if needed — extension is free.
4/15: Q1 estimates due. Prior-year IRA and HSA contributions must post by this date. Roth backdoor completed here for prior year if using pro-rata workarounds.
4/15. If you extend, taxes are still due — extension is to file, not to pay. Best time to review your CPA's positioning for the new year.
Track 750+ hours & >50% of working time in real estate trades. Half the year is your gut-check moment — pivot now if you're behind.
6/15. Same rhythm — but a great trigger to update projections after Q1 results.
Cost seg pays best when done in year of acquisition. Studies take 60–90 days — start now for properties bought in the last 6 months.
Rent your primary home to your business up to 14 days/year tax-free. Requires written lease, comparable rates, board minutes.
9/15. Estimates + extended 1065/1120-S deadlines land the same week. Also the last comfortable time to change entity/comp structure this year.
Hard stop for personal extensions. SEP-IRA contributions can still count if 1040 was extended — biggest retirement lever remaining for 1099s.
6 weeks before year end is the last realistic window to place equipment in service (§179 / bonus depreciation), buy real estate, or restructure entities.
Assets must be placed in service (not just ordered) by 12/31. Also final Roth conversion, DAF funding, tax-loss harvesting, HSA contribution.
Convert traditional IRA → Roth when income dips (sabbaticals, business losses, early retirement). Once done, cannot be reversed.