re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Actually both Cal 2-27 and Pearson 28 were at RYC, and Cal 29 is still at BYC until tomorrow, so I visited there a few times. The club and the harbor looked very nice and active, lots of boats, lots of events it seemed. I was there on the day of their season-ending halloween regata and it looked like lots of fun, lots of costumes, a live band cruising around the docks.
Unfortunately, I live in Cupertino, right next to San Jose, it takes me over an hour to get there without traffic, so for now I'm planning to get a slip at Coyote Point in San Mateo, about 30min drive and I'm hoping somewhat within reach of the Gate. Next year I'm thinking of moving to the city, if that happens I'll have to look around for something closer to all the action, RYC would definitely be high on the list.
If you find yourself back in the area, drop me a line. I'd love to thank you in person for all the good advice.