When I was based in OAK I lived in Alameda and loved it. If you get some roommates and look thoroughly, you can find an apartment in the $600 range (per person). There are cheaper places to live in the area, but Alameda has a great small town feel with lots of bars and restaurants within walking distance, and is about a 10 minute drive to work. To answer your other question, unless a lot of pilots leave over a short span of time, don't count on upgrading in OAK for at least a year.