It's funny how many people say not to go north, or go to Hawaii first, etc., when that's generally just not feasible. This is not a trip to be taken lightly but you would think there would be more information out there on how best to do it and what to consider to be increase the safety factor. The first thing is to find experienced crew, preferably two, and pick your weather window. If you have to do it on X date, it might turn into a very rough trip; at worst, it could turn out very badly. On my trip, we got pushed along with a light southerly wind (even flew the spinnaker a short time) and the seas around Pt Conception (which we hit at 0700 after leaving Santa Barbara around 0230) were glassy smooth. So, it can be great; it can also be horrendous. Two nights before, the wind was ripping through Pt Conception at gale force. There are some good suggestions about weather links and other info on this previous post (Sailing up Coast of California
). Latitude 38 has a crew list. You might find someone there. Ask around. You will want to have someone who knows what they're doing when crossing the shipping lanes, how to keep watch at night, and where to seek shelter. Be flexible and willing to wait it out for the next weather window. Make sure your boat is sound and has necessary equipment. Having radar and AIS increase the safety margin. Good luck and fair winds!