On several occasions I've wanted to introduce people to Eliezer's writings (and OB/LW aswell), but due to its disorganized and heavily-dependent-on-other-material-in-a-great-messy-web-like nature, I have feared that just a "hey check this guy out" would most likely just result in the person reading a few random essays, saying "yeah I guess that's pretty interesting" and then forgetting about it. Right before LW launched, I seem to recall Eliezer talking about how the LW architecture would allow better organization and that maybe he would do something to make his material more accessible. I haven't heard anything since then, but if something like that would be done I think that would be great.
(sorry if I'm being rude by focusing on just Eliezer's material when we're discussing the greater LW picture, but this is just a situation that I've found myself in a few times and I think it's still relevant to this topic. I also second ciphergoth's point about the elephant)
My original plan was to organize things into sequences, but I now think that converting to a wiki/post model (concepts defined in wiki, which organizes posts, which link back to wiki) is an even bigger win, though sequence browsing would still be nice.
Thing is, while I was actually writing all this stuff, I needed to just focus on writing it, as much as possible, even at the expense of usability - and go back and fix the accessibility afterward. It's not optimal but it got the job done.
This has been discussed some, but I don't think it's been the sole subject of a top-level post. I want to find out other people's ideas rather than driving the discussion into my ideas, so I'm asking the question in a very general form, and holding off on my own answers: