Classes vs Racing, and other thoughts
First, I am biased...
I think classes are an excellent idea for most, maybe almost ALL of us.
While I personally prefer USSailing courses over ASA, either, or any "strong curriculum and standards" class will help greatly.
This is mostly because such classes have a clearly defined body of BOTH knowledge and skills, whereas "On-The-Job" does not. For example, a disappointingly large portion of us do not really know how to Heave To, many have at least heard the expressin, but can't even define clearly what happens to a boat while Hove To. However, Heaving To is one of the most helpful skills of sailing, not just for really rough stuff, but also for simple things like stopping for lunch between races. It works best for full keel boats, but can be done, at least to some extent, with deep, high-aspect fins or even a high-aspect centerboard, like my current boat. I can, kind of, heave to in this boat, but probably would NOT have been able to LEARN how on this boat, at least not without a "coach" or "Instructor".
A diffferent example (and contrary one) would be using a rolling hitch and crossing over to an opposing winch to clear an override on a jib sheet. THAT one, I learned from READING and have not seen in any curriculum. The first time I used it, I was out if fairly stong stuff on someone elses boat. He got a SEVERE override and could not get it undone, period. I stepped up, put that rolling hitch several feet up on the offending sheet, then routed around and across to the other primary. A few cranks and the offending sheet was loose at the winch and the override was easily removed.
E.g., there is great value to BOTH reading or other study AND formal, structured classes. I have learned much from both. I suspect, well actually, I have NO DOUBT that I could learn embarrassingly much today from an ASA or USS sailing 101 course.
As to racing, it IS a great way to add significantly to cruising pleasure! I am a CRUISER who occasionally races. Thanks to what I have learned (formally and informally) from racing, I much more easily reach my cruising destinations with less effort along the way, and can easily and confidently decide on side trips, etc as I KNOW (at least roughly) what it will take to reach pretty much any given destination.
So, to me, even lifelong sailors can benefit from study (formal or informal) AND from skills practice sessions.