There's an old joke that goes something like "He doesn't have 10 years of experiance, he's had 1 year of experiance 10 times". Meaning that experiance doesn't mean much unless you can learn and build on it.

I think most of us approach sailing as sort of a rules-based game. We learn settings and tactics from books and other sailors (who in turn learned them from books or other sailors in a chain all the way back to the few greats of the sport), and while there may be a little gee-whiz explanation that goes along with those rules we learn, most of us don't really have a good feel for the "big picture" from which these rules are derived.

Since someone brought up the skiing analogy, there's a term in that sport called the "perpetual intermediate". That's a condition that many skiers get stuck in where they can't improve just by further experiance. They're in a local maximum where in order to improve they need to learn a new style which (at least in the short term) feels unsafe and uncomfortable. Maybe there's a similar local maximum in sailing where you have to go from learning rules to figuring out the rules for yourself.

I think the person at the top of the class is the person who figured out the rules. Most of the rest of the fleet is copying the leader. The difference between a good sailor and a great sailor may not be that huge in terms of elapsed time because the one can just follow the other. But it's awful hard for a good sailor to get in front of a great sailor.