For self-managing owners of 1–3 rentals
Key & Acorn's agents draft guest replies, schedule turnovers, and dispatch vendors — you approve every call. Each hour and decision lands in a contemporaneous log, timestamped as it happens, alongside everyone else's hours.
Key & Acorn is software, not a tax advisor. Qualification depends on your circumstances — your CPA makes that call.
Found us searching the so-called “STR loophole”? Your CPA calls it the short-term-rental tax strategy — Section 469, the 7-day average stay, the material-participation tests. We build the record it depends on.
Agents draft guest messages, schedule turnovers, dispatch vendors, and track maintenance — then bring you the call to make. Self-managing stops feeling like a second full-time job, without becoming the hands-off arrangement that undermines your position.
Courts have rejected after-the-fact logs as a “post-event ballpark guesstimate” — and your cleaner's hours can defeat your claim if you can't show yours were greater. Key & Acorn timestamps your hours, your decisions, and everyone else's time as the work happens, then exports a CPA-ready package on demand.
The 7-day average-stay rule, the 100-hour and more-than-anyone-else thresholds, personal-use limits — tracked live, so you know where you stand before year-end, not after. When losses qualify as non-passive, they can potentially offset W-2 income; your CPA makes that call with a complete record in hand.
The log isn't homework — it accumulates while you work. Here's the standing it shows you all year:
Every entry is timestamped when the work happens, categorized, and linked to its evidence — the invoice, the message thread, the photo. When your CPA wants the year, it's one click: entries, decisions, and everyone's hours, side by side.
Under IRS rules (Section 469 and its regulations), a rental with an average guest stay of seven days or less isn't treated as a passive “rental activity” — so if you also materially participate, losses can potentially offset non-passive income, including W-2 wages. It's not automatic: you must actually meet one of the material-participation tests and be able to prove it. That proof is what Key & Acorn builds. Whether the strategy fits your situation is a question for your CPA.
The regulation technically allows “other reasonable means” — but in practice, courts have repeatedly rejected records created after the fact as a “post-event ballpark guesstimate.” A contemporaneous log flips the burden: the record already exists, entry by entry, when questions come. Key & Acorn's log is created as the work happens, because that's when the product is doing the work with you.
That's the right question to ask — and it's the design principle of the product. Agents draft and prepare; you review, decide, and approve, and the log records that you did. Compare that with tools promising your rental “runs itself” or that AI will “act, decide, and execute on your behalf” — convenient words that cut against a position built on your participation. Key & Acorn is deliberately a copilot, not an autopilot. Ask your CPA how logged decision-making fits your participation picture.
Hiring help doesn't automatically disqualify you — but under the most-used test you need more than 100 hours and more hours than any other individual, including non-owners like a property manager or cleaner. Courts have ruled against owners who couldn't show others' hours at all. That's why Key & Acorn tracks everyone's time on the property — yours, your cleaner's, your handyman's — side by side, so you can see the comparison all year instead of discovering it in March.
Yes, with a nuance worth knowing: legislation passed in July 2025 restored 100% bonus depreciation for qualifying property acquired after January 19, 2025 — replacing the old phase-down schedule you may still see cited in older articles. The material-participation and average-stay requirements are unchanged. As always, timing and eligibility depend on your facts; confirm with your advisor.
We're onboarding a small group of self-managing owners first. Launching for the 2026 tax year.
One property or three? Tell us and we'll tailor your invite. Key & Acorn is software, not a tax advisor. Nothing on this page is tax advice; qualification depends on your circumstances. Talk to your CPA.