I think you're actually a bit pessimistic about weather in the bay area! I've even contemplated taking fenders off of my bikes! I moved here in July, 2012, most recently from Albuquerque, NM, but I've also lived in Arkansas and Pennsylvania. This place is just barely wet enough to sustain life and the temperatures are extremely mild, but change just enough to have seasons. Lots of amazing day trips to beaches in the south, SF, all the little cities in the southern peninsula.
Yeah, Specialized and Bell Helmets are in Morgan Hill, which is nice riding country, and Look's American subsidiary or whatever is located near me in deep south San Jose.
It is true that the cost of living is ridiculous. All the online calculators told me I'd end up paying 3x the rent that I did in Albuquerque to compensate, and I did, but I guess the "average" home here is much nicer than anywhere else I've ever lived. Here I get "wood inspired" flooring, in-unit laundry and an extra bathroom by comparison. The place I live in would probably be about double the cost if it were north of here, towards SF, and triple or so in SF itself...
I love Berkeley, too. I just helped a buddy move there last weekend. The east side of the bay is about 25% cheaper than here in SJ, which is why I'm hoping I get the job I'm in the running for in Fremont, which looks to have great riding, too.