Re: Is it prudent to have a kicker?
I do agree on the anchor in general, but a good bit of that area is better than 20 fathoms. Unless you're carrying several hundred feet of rode, you're going to be AWFULLY close to the shore before you have a chance to set an anchor. Also remember that "close to shore" is not necessarily safer. Sea room gives you more time before you go aground, and some of the shoreline in this area is anything but a gentle landing. North to Bodega, it's mostly going to be rocks and cliffs. You're almost always going to have winds from the west, so you're going to be drifting toward shore if you loose the engine.
Another thing to remember is the fog. It's never far offshore in your area, and it can move onshore with very little warning.
I've got a 19 foot Bayliner cuddy now, and I think trying to sail the main bay with anything like it (especially the "Slot" between Angel Island and Alcatraz) would scare the living bejeebers out of me. Withe the huge cockpit and only a couple feet of freeboard aft, one good wave over the stern, and you'd be trying out the floatation the hard way. I'd prefer something with a self bailing cockpit. My old Columbia had a pretty good cockpit drain system, and I can remember really NEEDING it on the main bay. In one case, I was below using the head as we passed under the gate on an outgoing tide, and for a second or two the "unfloodable" dorade vent just above the head was pouring a full stream of COLD water on me. That vent was on top of the cabin a good four feet above the waterline. I'd think you really want a boat designed for open ocean. Most of the cheaper cuddys (Bayliner, Searay, etc) are really designed for sheltered waters.
I'd really recommend you find someone with a good ocean going boat to take you out into the areas you want to boat, to really get a feel for what challenges you'll be facing. There's a magazine called "Latitude 3" that's distributed at most of the marinas in the area (it's also on line), and there are generally quite a few folks looking for crew.
On a positive note, as long as you have the right equipment and the right skills, the Bay Area is absolutely a GREAT area to boat. Again, I can't say I'm an experienced open water sailer, so please take this advice for what it's worth.