Winter is a stress test. Spring is when you read the results. An hour outside with a notepad will find nearly everything that is going to cost money this year.
The walk-around
Gutters and downspouts, because a blocked one is cheap now and expensive later. Roof edges and flashing, from the ground with binoculars if you have them. Fences and gate posts, which fail in wind and get missed until they are flat. Outside faucets and hoses for split fittings. Seals around doors and windows. Anywhere water has clearly run where it should not.
Write it down before you fix anything
The temptation is to fix the first thing you find and lose the list. Do the loop first, record everything, then triage. Half of what you find is a five-minute job, a quarter is a Saturday, and a quarter is a quote from somebody else — and you cannot tell which is which until you have seen all of it.
A house does not fail suddenly. It fails on a schedule you can read, if you write it down.