Going offshore is indeed not such a bad option
Even when carefully picking pick the best time and weather window, chances are you will have to contend with strong Northwesters that can make quite a few of the harbors along the way inaccessible because of the bars. You then quite possibly face an extended string of tiring overnighters along what is essentially a lee shore with lots of traffic (plus chance of fog, thunderstorms, etc). If you have your boat well prepared for offshore (e.g. following the Korenman's excellent West Marine Cup manual and/or reading "My old man and the sea") you can give yourself enough searoom by going 100 - 200 miles offshore thereby allowing the crew to settle into a much less tiring passage routine while keeping a respectable distance to trouble spots such as Point Conception.Personally, I would not like to do this trip in a 30-footer because of the potential discomfort level and the difficulty of finding experienced crew members. Fair winds,Flying DutchmanRivendel II (Legend 43)