Are you familiar with SF weather in the Winter? I ask because many folks who are not believe, until they get there, that it is going to be warm al la L.A..
But no--it is often really cold and windy. Maybe not like Chicago, but enough that you may regret paying more for a convertible.
And, why do you need a car? The Wharf area is very congested and has very difficult, expensive parking. Take the Muni, or cabs. Much less hassle.