I'll take a stab at this one as a relative newbie and web developer/architect...

It's true that from an information architecture standpoint the major links on this site are not always self explanatory. That is part of the site's charm though. Wandering through the nodes is much like browsing through heaps of scrolls in a lamasery (pun intended) searching for perls (sic) of wisdom. Having said that, there is one minor modification that I would suggest.

I'd include the Guide to the Monastery node in the main navigation at the top of the page. All the other items in the Information section of the sidebar are already included the main navigation or under the Need Help?? node. This link seems to be the only one lost in the shuffle. After a user is logged in it is only available by scrolling past the lengthy, but useful, Chatterbox and Other Users sections.

I believe this would also address the original issue here which is the availability of descriptions for each section in the site. The Guide to the Monastery nicely summarizes each section in one central place. A quick glance through the list would certainly be helpful for new users trying to make an educated decision about where to post.