A 1920s house in town and a cabin a few hours away. Two sets of vendors, two insurance policies, two utility stacks, two property-tax cycles. The AI doesn’t run the vendors — vendors are humans. The AI runs me. The unlock is “nothing slips,” not “nothing manual.”


2026-05-16 — Homeowners renewal, three quotes in a week

Current carrier was about to renew but their underwriting couldn’t cover the ADU and detached structures properly. Hard deadline. Got three carriers to quote in one week — what would normally take a month of dropped balls.

The AI didn’t make the calls. What it did was: take notes from each call as I summarized it, keep a running side-by-side of the coverages, and stop me from re-asking the same question to the next agent. By the third call I was crisp because the first two were captured.

2026-05-09 — Seven solar panels making zero kWh

Seven panels on the roof producing nothing. The installer’s remote firmware fix didn’t work; an in-person service visit is the next step and they’ve quoted what feels like a lot for it. The thread has been going back and forth for weeks.

What AI is good at here: drafting the polite-but-firm follow-up email when the vendor goes quiet, and keeping track of “what did they promise on the last call, and is the new quote consistent with that.” What it’s not good at: making the actual repair cheaper. That part is a human-to-human negotiation I haven’t enjoyed.

2026-05-07 — A ballot showed up

Got a Prop 218 mailed ballot for a new fire-service assessment on the cabin property. Roughly $475/year, indefinite. The deadline to return it is concrete (received, not postmarked) and the property is in a high-fire-hazard zone.

AI as a research intern: pulled the proposal docs, the engineer’s report, the district’s last few audit reports, the alternative service scenarios if the measure fails. Output was a one-page yes/no recommendation with the strongest counter-argument honestly stated. Took about two hours. The decision is still mine; the homework is done.

2026-05-03 — The cabin runs on a checklist nobody used to keep

The cabin is 150 miles away. A caretaker handles on-site work, a cleaner handles turnovers, plus the usual utility/insurance/propane/internet stack. Used to be: things slipped, I’d find out three months later when a bill bounced or an inspection went out of date.

Now there’s a project file that knows: next caretaker visit, last cleaner visit, current outstanding invoices, expiring policies, deferred repairs, seasonal deadlines (weed-whack before fire season, propane before winter, tree pruning around PG&E line work). AI doesn’t do any of those — it just doesn’t let me forget any of them.

The genuinely freeing thing isn’t automation. It’s that I stopped carrying the list in my head.