Tagging onto what everybody above has said about year-‘round sailing, that is true and that’s a good thing. New England in the winter is really cold (read: Icy). Northwest is not quite as cold but cold enough, a damp wet cold, and for a very long time. The SF Bay winters may get cool and give some wind chill but it’s still do-able and the summers will be nice to hot, but hot depending on where one is. Near the Gate it will typically be comfortable in the summertime and the further inland, like the delta, the warmer it will get. One nice part is you can pick the lemons off your own lemon tree on New Year’s Day.
Summer winds are typically light until the fog burns off then they pick up as the valleys warm up. Do the windward sailing in the morning or the evening.
Sails: the typical OEM sails will get blown out and with the increased draft make the boat tender. The solution is for heavier or stronger sailcloth and shallower draft. A fin keel vs. a shoal draft is a plus, especially for going outside, but that isn’t to say a bulb-wing keel won’t work, just say’in that my preference is for fin keel.
Several years ago I went out on a H43 with sails that were blown out and it was no fun. The boat would heel over and we just couldn’t get it to sail well, felt really tender. On the other hand, I crewed on a Cal 40 out of St. Francis that had good (flatter cut) sails and it sailed really well, so big difference in how they could handle the afternoon wind.
Winds are much more predictable than up here. One[ce] you learn about the weather patterns it’ll be pretty easy to trip-plan and stick to it which will probably make the crew happy ‘cuz they can plan and know what to expect. Up here, “things change” and it drives my wife crazy because it didn’t turn out as she expected when I have to take a different route or go to a different place.