Your odds are much much better starting in SF and riding south. The winds would be contrary only in advance of the approaching front. Also the weather typically improves as you move south. Our storms typically come from the N Pacific and get weaker as they move south and east across the state (unless we get a "pineapple express" condition channeling moisture from southwest over the state). But we haven't had that condition in a long time.

It's unlikely you'd be washed out for a week. Not impossible, sometimes a low will stall over the the state and just keep bringing moisture, but the typical system passes through in a day or two. Just a question of how much of a gap or how much high pressure is between them as to how much time between storms.