Yes, cool thread. I'll be watching this for updates. I am in a somewhat opposite position. I have many many years of 16-20ish foot powerboat experience, but until the last few years I knew nothing about sailing minus the fact I liked it. We went for formal ASA bareboat training and started dinghy sailing.
I was very happy with what I got out of my school but I also understand your position. Go slow, you'll be fine. The fact that you are thinking about your approach of getting experience shows you aren't rushing into something crazy. Good luck to you with your new ride.
Go sailing now my brother,
It's later than you think.
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