Doing this before leaf drop rather than after is the entire trick. Everything is reachable, the weather is pleasant, and you are looking at bare gutters instead of packed ones.
1. Gutters and Downspouts.
Clear them, then take a hose to them and watch where the water goes. The important part isn't the gutter — it's the last three feet. Water landing at the foundation is what shows up as a wet basement in March. An extension that carries it a few feet out is cheap and does more than almost anything else on this list. If a gutter has pulled away from the fascia or a downspout has come off its strap, that is a much smaller job now than it is with forty pounds of wet leaves in it.
2. Doors That Suddenly Stick, or Suddenly Don't.
Wood swells through a humid summer and shrinks back once the heat comes on and the air dries out. A door that has been binding since June may free up on its own, which is worth knowing before you plane anything off it. The reverse also happens: a latch that was fine all summer stops catching once the frame moves. That is usually the strike plate, and it is a screwdriver and a file.
3. Weatherstripping and Thresholds.
Close the door on a piece of paper and pull. If it slides out with no resistance, the seal isn't sealing. Do it at the top, the middle and the bottom of each exterior door, and at the latch side and the hinge side. Adhesive-backed foam that went on a few winters ago has usually given up by now.
4. Hose Bibs.
Disconnect the hose. That is the one that matters — a hose left connected traps water in the bib, and a frozen bib splits inside the wall where you won't see it until spring. If you have an interior shut-off for the outdoor line, close it and open the bib to drain.
5. The Roof and Flashing, From the Ground.
You're not going up there. From the ground you're looking for lifted or missing shingles, and for anything loose where the roof meets a wall, a chimney, or a vent. Binoculars are a genuinely good tool for this.
6. Anything That Will Be Under Snow in Three Months.
Steps and handrails come first — a loose handrail is a minor repair in October and a serious problem in January. Then the walkway, the outdoor lights, and the shed door that hasn't shut properly since spring.
Most of that is a Saturday. The ones worth calling someone for are the ones on a ladder or a roof — if that's where your list is headed, Connected Craftsman is a call away at (484) 699-0626.