One thing that could help new users dive into Less Wrong would be to make some reading recommendations based on reading difficulty. (I'm including some things not hosted on LessWrong.com when they're very LessWrong-ish and written by leading LessWrong authors.) For example:
For everyone
- Yudkowsky, Harry Potter and the Methods of Rationality
- Yudkowsky, Twelve Virtues of Rationality
- Yvain, The Worst Argument in the World
- Yudkowsky, Reductionism
- Lukeprog, How to Beat Procrastination
- Yudkowsky, Technical Explanation of Technical Explanation
- Yudkowsky, Timeless Causality
- Yudkowsky, Bell's Theorem
I've seen "mathgoods" before. "Mathgods" must be even better!
But still nowhere near as awesome as superhero mathematicians.