What to do, when, and what to stop paying someone else to do.
Deferred maintenance is the most expensive thing about owning a house, and it never feels like a decision. Nobody decides to let a gutter overflow for three years. It just happens, and then the fascia is rotted and the bill is four figures instead of forty dollars.
The way out is a calendar rather than a to-do list. Here's the year.
Spring
The season for finding what winter did.
Look at the roof from the ground with binoculars, or hire someone. Missing or lifted shingles, damaged flashing around chimneys and vents, anything sagging. Don't climb up unless you're genuinely comfortable and equipped.
Clear the gutters and check the downspouts run water away from the foundation. Most basement water problems are roof water problems that nobody traced back.
Walk the perimeter. Grade should slope away from the house. Look for cracks in foundation and masonry, and note them with dates so you can tell later whether they're moving.
Service the air conditioning before the first hot week, when every technician in your city is booked.
Reconnect exterior faucets and check for splits from freezing.
Test smoke and carbon monoxide detectors, and replace batteries whether or not they're chirping.
Summer
The season for exterior work, because everything needs to be dry.
Caulk and seal around windows and doors. Cheap, unglamorous, and one of the highest-return hours you'll spend.
Paint and stain what needs it. Exterior paint is not cosmetic; it's the barrier keeping water out of wood.
Trim vegetation back from the house. Branches on a roof, shrubs against siding, and vines on masonry all hold moisture where you don't want it.
Clean the dryer vent all the way to the exterior. Lint in a duct is a fire risk and it's easy to forget because you can't see it.
Before the first freeze
The season with the hardest deadline, and the one where being early actually matters.
Service the heating system. Same logic as spring air conditioning — do it before everyone else needs it.
Shut off and drain exterior faucets and disconnect hoses. A hose left on a bib is how pipes split.
Clear the gutters again after the leaves are down, not before.
Check weatherstripping on doors and windows.
Find your main water shutoff and label it. If you learn where it is during an emergency, you're already too late. Show everyone in the house.
Deep winter
Mostly watching.
Watch for ice dams at the roof edge — they mean heat is escaping into the attic and melting snow that refreezes at the eaves. It's an insulation problem, not a gutter problem.
Run water occasionally in rooms on exterior walls during hard cold.
Check the attic after heavy snow for signs of moisture.
What to do yourself and what to call for
Do yourself: gutters at a comfortable height, caulking, weatherstripping, filters, detectors, dryer vents, trimming.
Call someone: anything on a steep or high roof, anything involving gas, anything involving the electrical panel, HVAC servicing, and any structural crack that's changed since you last looked at it.
The test isn't whether you can. It's whether the cost of the worst outcome exceeds what you'd save. On a ladder at height, it usually does.
Keep this one. Set two reminders a year — one in early spring, one six weeks before your average first freeze — and this guide does the rest.