Hint first (sensitive people get it, and you spare their dignity) then be clear (most people get it) then be brutally honest (slightly dense people get it). If I have to resort to the 2x4, then I really have to decide whether enlightening this person is going to be one of those battles I choose or one of those battles I do not choose.
This approach is fairly good. It would help if you gave examples. Also, while their is a benefit to public disagreement, sending criticism as a pm can help the recipient save face. I usually do this when pointing out grammatical errors, like the fact that I used their rather than there. It might be worth mentioning this in the orientation.
Including a very abbreviated version of the Jargon file would probably be a good idea. At minimum I'd like for it to include what we mean be rationality. Preferably with a quick discussion of [http://wiki.lesswrong.com/wiki/Hollywood_rationality[(http://wiki.lesswrong.com/wiki/Hollywood_rationality), and that the word is "rationality" not "rationalism" which usually referrers to a completely different philosophy.
Proposed rewrites can be found here. Please suggest specific improvements in the comments!
Although long-time Less Wrong users don't pay much attention to the home page, about page, and FAQ, I suspect new users pay lots of attention to them. A few times, elsewhere on the internet, I've seen people describe their impression of Less Wrong that seemed primarily gleaned from these pages--they made generalizations about Less Wrong that didn't seem true to me, but might appear to be true if all one did was read the about page and FAQ.
The about page, in particular, is called out to every new visitor. Try visiting Less Wrong in incognito mode or private browsing (i.e. without your current cookies) to see what I'm referring to.
But the current set of "newcomer pages" isn't very good, in my opinion:
I certainly don't claim to speak for all Less Wrong users. If you have any thoughts, please comment here, send me a private message, or log in to the wiki and edit the candidate pages directly.
I'm especially interested in getting feedback on the FAQ, because I took the liberty of codifying some social norms that were previously implicit: see the section Site Etiquette and Social Norms, especially the bits about Discussion vs Main, politics, and "if you never get voted down, you're not posting enough".
If you think I codified the social norms incorrectly, or you've been thinking they really should be different, please comment! The FAQ seems like a good way to broadcast preferred norms, so I suspect this is an ideal thread to discuss them.
If you've got a suggested change that's nontrivial, I encourage you to create a poll for it here using comments as poll options or HonoreDB's system.
(Previous discussion.)