Excellent post, Merlin, I hope it helps anyone else out there who is contemplating learning to sail.
My viewpoint is that of an instructor. I occasionally teach sailing as a part-time gig, and am interested in students' feedback, so thanks, what you said rings true.
I agree that the best sailors come from small boats, so learn on the small sloops, then you can sail the big stuff. Not necessarily vice-versa.
And I also agree (mostly) that the only way to learn sailing is to get on the helm and sail. When I teach, I honestly try never to touch the helm unless it's a true emergency, which it almost never is.
I agree about read, read, read, with a small reservation: I think the reading can only take you so far, then you have to sail, and handle the helm and the sheets. Then read, now it will make more sense. Then sail. Then read again. Book learning will only take you so far, though it's valuable.
Would I guess correctly that you came out of Community Boating in Boston?? A great place. I learned how to sail a little north of there, and now I have the privilege of teaching way down south, on Lake Pontchartrain.
Best wishes, and thanks for an informative post.