no matter what. I've done a couple mid 40' powerboats north from the Bay area and Santa Cruz and big ships between the Bay area and points south as well as regular work 200 miles offshore off SoCal.
It's windy. It's coming from the exact place you're trying to go to. That said, one trip (April, I think) was pretty mild and flat between San Fran and the Columbia river bar.

You've just got to have time either way. Time to wait out weather. Time to rig/unrig/schedule for a truck. Greg's comment regarding cost to adequately prep and equip for such a passage versus putting it on a truck is probably the higher of the two.

I don't remember what size/type of boat you've got but it probably doesn't matter as none will be comfy. Hate to be negative on this one but, whenever I think of it, well, I pretty quickly think my way out of it soon enough.