Quote from CalTrader:
Lived in Redwood City a few days a week a couple times a month in a nice apartment on my clients tab while doing work there in 2001-2002. Redwood City was a hole IMHO: I would never live there - 1600 sq ft houses go for 700 - 900 K. Many of the technology companies had their import recruits living there in company financed accommodations. I finally told this client it wasn't worth it for me to be working on their account if we had to spend time - even a few days - in redwood city. They re-negotiated and we do all the work from So. CA. now. Also my wifes employer - rather than lose her - allowed her to work from So. Ca. Other than SF and marin and a few communities around Stanford, the bay area is not a high quality place to live - and certainly not worth a premium IMHO.
You don't know the Bay Area well then. Yes, anywhere down near 101 is a hole, but there are many many absolutely gorgeous towns/communities in N. Cal. Inland from 101, ya have those you mentioned, plus Portola Valley, upper Burlingame. Down south Saratoga, Los Gatos. Santa Cruz if you can handle the hour comute. Most of the east bay is super nice once you get away from the bay. Many parts of SF itself, ALL of Marin. This area has so many lush green beautiful neighborhoods its mind boggling. Unfortunately, infrequent visitors usually see the worst places possible.
Basically, the flat areas around the bay suck (except for SF and Marin), but many, if not most away from the bay are great.
Jay