Spring: service the AC before the first heat wave (techs are half the price in April), clean gutters after the last freeze, walk the exterior for winter damage — caulk, flashing, grading. One $150 gutter visit prevents the fascia rot that turns into a $4,000 repair.

Summer: irrigation checks, pest barriers, and the annual unit walkthrough. Look at supply lines, water heater age, and caulk lines while everything is dry and accessible. Fall: furnace service before the first cold snap, weatherstripping, and a roof look-over while repairs are still scheduling at normal rates.

Winter: it's pipe season. Make sure tenants know which faucets to drip, where the main shutoff is, and that 'the heat seems weak' is a same-day message, not a Monday one. The cheapest insurance you'll ever buy is a tenant who knows where the water shutoff is.

The trick to actually doing all this is recurring scheduling. Set each visit up once with a pro on your bench, and let the calendar fire the jobs — no remembering required. NiceList's recurring services were built for exactly this rhythm.