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Aloha Adam,
Welcome aboard! There are many boats at a better price south of SF. Trailerables go up to about 26' in length and in my opinion this is too small for the SF to SD sail. My sail from SF headed to Hawaii in a 38 footer got derailed by weather damage to the gooseneck on the mainmast. We handn't even gotten to Pt. Conception which has some whicked reputation.
You can buy specialty trailers for any size boat but they cost quite a bit more.
You can't just anchor anywhere coming down the coast because of the seas, weather and shoreline so it is only safe to pull into harbor then anchor or find a vacant slip. Watchstanding and provisioning become necessary anytime you go overnight. You have to sleep sometime and by COLREGS you must keep a watch at all times.
This exercise that you are going through is a learning experience. Don't be discouraged in what you hear. Just learn as much as you can and be safe.
Kind regards,
JohnL
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