re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Yes, that is what I'm guestimating. I'll have to start early to peek out of the Gate, but it is still better than about 5 hours out of Redwood City. The next harbor north is Oyster Point, and that would be close to an hour drive... There's also Santa Cruz and Half Moon Bay, but ocean sailing is a little out of my reach just yet. As I said, if you know of other options, I'd appreciate them.