I only have to worry about the change once a year as far as major things go. Which is what I was alluding to.

Comfort levels? I usually wear a hoodie with 1-2 layers down to 32, then my coat for everything below that with layers added the colder it gets.

I live in Michigan so the transition seasons are a crap-shoot on what you'll need to wear that day anyways so I have to keep clothes in my car either way temperature is measured.