re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I do not know what side of the Bay you are living on but one Club to investigate is (click on) Richmond Yacht Club
Your contact there would be Antonia Vanoni at (510) 237-2821. She can/will be happy to introduce you to some of the members and get you acquainted with folks. RYC is a real sailing club--both racing and cruising--and the members are very friendly and helpful. We have been members since the mid-1970's and maintain our membership even though we now live in southwest Florida. Never the less, we still display an RYC Burgee on our Transom (crossed flags) and will occasionally race under the BYC Burgee. If you're interested send me a PM.
PS: RYC has an excellent yacht harbor by the way, and quite affordable.
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."