I learned to sail(?) this past year at Harbor Sailboats in San Diego. AsA classes. I'm content on the $75 Capri J27's. I'm still trying to get out of irons all the time. I can rent up to a 38 iirc but $350 for weekend.
Walking the docks-- I thought I would have to pay 45k--65k. Min. For a bareboat.
My wife owned a Morgan hull#1 "Rage" 54 that won SF to Hawaii a couple times so her idea of a weekender is a Swan '47. 400k
We enjoy sitting in the clubhouse hot tub at the end of a day in Harbor Island, drinking wine and watching all the pretty ladies in their slips.
I look forward to reading your post after you go out again and if it comes right back. What a legendary area you live in for sailing.