[charlesbahn]

Oh Boy, something I know something about. First, the cost of a boat is only the beginning- just like a Porsche. The upkeep is $$$ even if you do it yourself. First, you have to decide if you really like sailing. Especially important is your SO. Take courses, hang out at the marina, ask ?'s and get invited on other's boats. Make sure you and your mate don't get sea sick, and don't get sick of each other in small places that can become stressful.

For your location and desires, I would think that something like an Alberg 30 would be a good choice. Older design but full keel and very seaworthy. Stiffer and slower than a Catalina 30, but in my opinion a more seaworthy design. A very good boat for SF where the winds blow pretty hard. I'm biased though, I sail an Alberg 37 (yawl).

A good boat to just day sail and learn in is a Flying Scott. Good performance and hard to turn over. But if you reallly want to learn to sail well, start small, in a harbor rat- a small sailing dingy like an Optimist. Very exciting and if you make even the slightest mistake you learn quickly because you go swimming.
Have fun, and Fair Winds.
Charles