I know I am beating a dead horse here, but SF is really expensive. Everyone I know that lives in portland loves it. I am not sure how people deal with the crazy amount of rain that is up there. But everything I've heard about the city is nothing but great. From public transport, skating, women, booze, weed, women, weed, skating, booze etc. It's all good. SF has the same though, but at a lot higher cost. I lived in the east bay for 3 years and thought of moving to SF several times, I would never have been able to enjoy the city had I lived there. Meaning I would have been spending so much just to live, that I couldn't have afforded to go to a bar or buy a bag.
My vote is for portland.