Wisdom seems to be basically successful pattern matching of mental concepts to situations, and you need life experience as the training data for mental concepts, the varieties of situations, and the outcomes of applying different concepts to different situations to get it running at the sort of intuitive level you need it.

I think Moldbug is somewhat on target, LW doesn't really have much in the way of either explicitly cultivating or effectively identifying the sort of wisdom that lets you produce high-quality original content, beyond the age-old way of hanging around with people who somehow can already do it and hoping that some of it rubs off. So we get people adopting the community opinions and jargon, getting upvotes for being good little redditors, not doing much else, and thinking that they are gaining rationality. We haven't managed to get the martial art of rationality thing going, where there would be a system in place for getting unambiguous feedback on your actual strength of wisdom.

Prediction markets are one interesting candidate for a mechanism for trying to measure the actual strength of rationality.