I think I'm being dense, but I don't really understand your first point on the searching. Not sure the hangover is helping.
Oakland is connected to the BART which is the metro system for the Bay Area. Not sure what the journey time is. However, it would seem that there is a perception problem. The same kind of perception trend that led Ryanair to serve main airports as well as/instead of minor airports. Where Ryanair only used to hang out in Hahn they now fly from Frankfurt-Main; Brussels Zaventem as well as Charleroi. Apparently the same trend is kicking in at Oakland.
Premium cabins is of course the killer. I remember when Oakland started, all the marketing was focused on Oakland being very close to the wine valley, chasing premium end tourism to the vineyards etc. However, it doesn't seem to work. The same kind of model led to starting Cape Town, which is premium tourism heavy, and seems to be working well. Perhaps the ratty 777 product on the Gatters fleet is not helping.