I may be asking for the gods to do me dirty, next time I sail up the coast, by saying this but I have been up the California (LA to San Francisco) 4 times on my former NorSea 27. It was painless (but boring) every time!. Those same trips up were preceded by a great sail down. I sure would not have wanted to go up the coast in the weather I had coming down. I think this was a combination of luck and the time of year I did it. I spent one night at Coho anchorage and slipped around conception in the early morning calm. You can sit in the anchorage and listen to the weather
radio to know when things are calm out around the cape. It is not easy to tell from the conditions in the anchorage.
Every time I took the boat up I did it over labor day weekend and had three days of dead calm to motor in.
There are several places you can duck into on your way up (depending on conditions). You can stop at avila beach, moro bay, san Simeon, still water cove, santa Cruz, and halfmoon bay. Some of these anchorages are exposed to the south but if its blowing from the south you thank the powers that be and keep sailing.
I dont see the problem with an 11 hp engine...If it will push the boat in calm conditions it should do the job. If conditions conspire against you, turn around and head for shelter.
The longest jump on the trip is from San Simeon to Stillwater cove...That is about 97 nautical miles.
You can leave your boat at avila beach, moro bay and monterey or santa cruz. BTW, santa cruz harbor closes in strong southerly conditions but monetrey would be a choic in that case...
So as to the trip up, I''d try for the bubble of calm that seems to persist for a few weeks at the end of the summer, get a few good books, and have your
autopilot steer while you just putt putt your way to SF.
SF bay, as one of the two natural harbors on the coast, has lots of marina space and prices are cheaper than in southern california. There are very few livaboard marinas on the penninsula more are on the east bay side.
One of the free sailing rags (Latitude 38 or the log) puts out a "slips" directory every year that should help. I think one of the cheapest marinas around in Marina bay in Richmond. Dont know what their livaboard policy is. Another one I would try is the San Leandro marina. Last time I was there they had a lot of empty slips.
Alameda is a great place to live and is frequently sunny when the city is fogged in.