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
For those with some math and statistics
- Yudkowsky, Technical Explanation of Technical Explanation
- Yudkowsky, Timeless Causality
- Yudkowsky, Bell's Theorem
For mathgods
Now, I ask: What are some of your favorite articles in each of these categories?
I think http://lesswrong.com/lw/od/37_ways_that_words_can_be_wrong/ is a good starting point too, it summarizes a lot of important things and give links to details for each (in the "for everyone" category).
I consider diseased thinking to be an unofficial part of the sequence on words (of which "37 ways words can be wrong" is the hub). It gives an example for how words can influence our thinking that is not contrived, practical, not obvious and important. It's a nice example of clear thinking.