Hey Adam, my good buddy works for Apple and just moved from Cupertino to SF. If you can, live in the city and take Appple's shuttles to work, the city is a lot more fun than Cupertino.
The wake scene is awesome in northern CA!! You are an hour from the Delta and there are some lakes that get very crowded on the weekends. Basically you need to meet a crew and plan to ride the Delta, it is the west coast mecca of wake. Also, there is a new shop in San Jose, Liquid Playground. It is a Wakeworlder making it happen. http://www.theliquidplayground.com/