You're thinking too hard again. If you really have a lot of sharp junk in the road, or goatheds where you live, then trade up to a tire with Kevlar in it. Carry 1 patch, a tire lever tool, one wrench for the wheels. Air pump? Maybe, but unless you're out in the country somewhere there should be a filling station with an air hose close, so I don't bother with it. I've cycled for years now and I've never had a flat on the road yet although I'm sure my time is coming.

If it's cold enough for wool shorts, aren't you going to be cold from the knees down? Tell you what, try the basic kit for a week, then see what you think. When you actually get out there riding the route, you often find that what you thought you need--you don't! And then you figure out what you do really need.