Kettlewell's
advice lines up with my experience. Like you, I spent a life on ski
boats and small sailboats. I had a good grasp of navigation and
weather from aviation and that was helpful but not everything transferred. The biggest difference was that in an airplane I looked to get around
weather that seemed almost stationary. When making passages, it seems I am stationary and the weather is moving (hopefully around me).
I learned much faster by doing rather than the classes. Classes helped, but the doing was more necessary. Like river rafting,
learning judgment and technique is the key. Set acceptable risk levels low at first while to try to survive learning judgement (LOL).
Transitioning from small watercraft to sailboats wasn't that tough. I did some
bareboat charters until I bought my first "real"
monohull. I lucked out and bought a great
boat for my needs (a 44' catch), but I was truly lucky and ignorant. Doing it again, I think I would have purchased something smaller at first and then
purchase the "dream" boat a bit later.
In any case, you're on a fun journey.