I'm from the west and I liked NYC at first sight, although I think it'd probably be a bit much for me long term. Boston, though, was fantastic. Now I'm in the bay (still in temp housing, deciding where to live), so we'll see how it goes.
On the subject of horrific first impressions, though, Bangkok definitely fit the bill for me. Perhaps not as big as NYC, but dirtier, crazier, far less organized, everything in Thai (a problem for me, not for them), dogs everywhere, not just bums but homeless starving mothers with a little baby kneeling in the gutter, bugs... jesus, that was an experience.
Also, I take it you feel the same about Mountain View? Anything closer than San Mateo that you feel has character? I'm working in MV, and I'm not a huge fan of long commutes.
Do you think downtown MV (Castro St, etc) is any better? I actually just moved to the area myself, but haven't found my own apartment yet, so this is quite pertinent for me.