We have decent rail service (Cal Train on the Peninsula and BART on the east bay) to get around, and of course people do drive. We've got both public and private schools that are considered top schools in the country, and of course there are failing schools as well. Our state government is pretty dysfunctional at the moment. Oh and the weather is really really nice more often than not. Oh and if you go north of the Bay there are a bunch of great places as well from Sausalito to Novato to Petaluma to Santa Rosa.
There is so much variety then the nine bay area counties that its been called its own country by tourists.
There are places where it is expensive and there are places where it is moderate, in general housing is a bit hard though because when a company goes public and mints a bunch of millionaires or nearly millionaires there is a brief run on housing as people go out, buy a house, and convert a variable priced asset into a fixed price one. Generally though for the same money the houses here compared to Chicago will seem like a big downgrade. ( I know two folks who went the other way, Bay Area -> Chicago, and they were quite thrilled )