I think the length and varying tone of this thread has proven than you need a more inviting source for beginners. :)
And dare I say it, but forums could be used also. Apple's discussion forums are quite successful simply because they don't use email. Beginners can search, peruse and respond then they feel like it without having their email fill up with, hmm, 46,000 emails over 3 years :)
Forums require much more participation by the helpers, as they are nowhere near as convenient to read serially, but the software I use can be set up to email moderators with every post.
Also the Apple board do not have any responses by Apple employees, rather it is wholly users helping users. They have reward systems such as ranks, post counts, etc. Some users eat this up. Thus you prime the pump with the "experts" and then then groom helpers over time.
Unmoderated forums can also become a huge mess of content. That is the downside of having content archived automatically. Compared to the current method of squeak-dev archives (not searchable online from what I can tell, just downloadable in chunks), though, the cost of too much content might be outweighed.
Plus you can moderate forums as well.
Toss in a "Lounge" an all of the off-topic stuff immediately has a home.
Anywho, had to throw that into the mix. Sometimes helping a different set of people requires different tools, so something to ponder on!
Steve