It's true that LessWrong could have more focus on catering to newcomers as opposed to catering to people who've been here for months; which is to be expected when most content (posts and wiki) are made by long-timers.

I guess the best approach for newcomers for now is just to show up and talk to people (like what you're doing now!) - not as smoothly organized as having a formal system, but at least it's a self-correcting process that adapts to the quirks and interests of people better than a pre-programmed self-assessment system could!