Re: Should I spend thousands on lessons, or....
Don't go to the Thelma and Louise flying school, it's a short trip with a surprise ending.
Depending on what type of learner you are you may want to take some classes if you decide to get serious on cruising as opposed to day sailing. I don't mean ASA classes, I mean local community college classes on diesels, electronics, and other stuff like that.
Diesels are diesels, no need to take a Yanmar class so you can work on a Volvo.
Lessons learned are opportunities earned.