I sailed many time as a kid on bays and the Gulf in small boats. Didn't sail again for 30 years or more. Decided I wanted to do it again. Took an ASA class to relearn skills, sailed on OPBs then about 4 months after I restarted, I went boat shopping. 6 to 8 months later i fell in love with a huge 44' Mason. Love it. I would never buy a small boat, it think it is better to rent one or use OPBs (that is if you are planning on a liveaboard or big boat).
I think it is all in your comfort level and how quickly you learn the basics.
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