Interesting thread. The posters came at this thru different venues, but there are commonalities in the result.
FWIW.... we wanted to learn to sail, and tried to start out with a well used Lido. Discovered that neither of us liked hiking out. Sold that and bought a new Ranger 20 in 1976, and most important, joined the local fleet.
This put us in touch with a lot of other couples and with the informal weeknight racing got us on the water a lot. Then were were weekend gatherings and picnics at nearby islands. Meetings, sometimes with speakers. Winter parties for the off season.
While I had rowed around in small fishing boats as a youth, I had no sailing experience. I did read books, tho. For shear enthusiasm the Arthur Ransome series of novels are perfect for any young person.

Most helpful technical book was "This is Sailing" by Craigh-Osborne (sp).
Suspect that some of us may have, perhaps by an accident of genetics, more "wind sense" than others, also. Perhaps.
I recall that early on, I noticed that some skippers would unconsciously turn their boat when they turned their head.... and I weeded out that response from my actions. Lots of subtitles in sailing!
Also learned that I really enjoyed light air racing, where every nuance of trim and course study needed to come together.
In general, the local OD fleet was a huge part of our experience, and soon we joined a small YC, and cruised and raced a lot with them. We did stick with OD racing and then Level Racing when we bought a larger boat.
Tried handicap racing and disliked it, quite a lot. One Design (OD) racing is absolutely the Best for quickly growing skills... By Far.
Like others here, I am also leary of skippers with paper certifications. It seems to be of value for some, tho.
Speaking of boating in general, I also learned a lot from several decades of deliveries offshore, and recommend this, in general. It will seldom involve a lot of sailing, but the operations of different boats and systems is quite valuable. The lessons in human nature are illuminating, as well....
