I don't see this is a potential future achievement of LW (or CFAR), primarily because others are already doing it much better. In the lead here is Khan Academy, with the knowledge map dashboard (last link, might need to login first), with tons of data and progression based on complete mastery of a topic, with time-spaced reviewing and nifty features all the way up to achievement badges for the positive reinforcement and social bragging rights.

I also hear Coursera is planning to continuously upgrade their personalized-feedback mechanisms, possibly up to the point where the system might automatically detect that, while attempting to solve these integrals, you're struggling with some particular type of factorization method, and then snap you back to the specific relevant modules and make you master them before resuming calculus. This seems like the natural next step from Khan's current system, and would be such an incredible distance in quality up from standard high school classrooms that I have a hard time putting into words how amazingly awesome that feels for me.

Basically, LW could help with specific courses, possibly with regards to Bayes stuff or applied epistemology or decision theory, but if we tried to tackle getting-people-to-like-and-be-good-at-maths, other experts already have a large lead and are doing quite a good job of it; our impact would be marginal, and we can achieve much greater things in other domains than standard mathematics.