What length of routes are you looking for? I think you're probably looking for a bit more of a challenge than the previous thread starters on SF routes. Feel free to PM me if you'd like me to email you some route sheets in the southern Marin area. You'd just need to make your way to and across the Golden gate Bridge.

I think your change of cassette will probably be good. Weather will be anything from 60's and foggy in the city to 80's in Marin. Arm warmers, vests, etc. that allow for adaptability of clothing are good.