...this site is a distributed effort and very much a grown wilderness...

I assure, you that is all very well understood. No misapprehensions there.

...it would be a bit like documenting which drawers in your room you put what stuff in - a lot of it is a matter of habit and some of ritual, so will necessarily seem obscure.

Perhaps, but that's not a reason not to do it. I don't believe anyone would expect that the extra documentation I am asking for would be any less obsolescent than any other aspect of the site. I.e. no one has unrealistic expectations. But again, that's no reason not to do it.

...just calling for "more documentation" is not going to change a whole lot.

And that is not what I am doing. I am asking for specific items of information in specific places.

Maybe any newcomers reading this would like to make a concerted effort of noting things down that confused them...
As always, precise questions are more helpful to all parties involved than generic ones.

I believe that is what I have just done, thank you.

And the solution to the problem I have highlighted is not for me (or some other luser) to put together his own personal index of interesting nodes. Many users have done that, and they're all (perhaps not equally) obscure relative to the front page. Newcomers to the site need to have an obvious way to find out what the sections of the site are for.

All it would take is from someone with power to spend 15 minutes annotating the main sections which are not currently self-documented. The ones I'm aware of are:

1. The Monastery Gates
2. Seekers of Perl Wisdom
3. Meditations
4. Craft
5. Cool Uses for Perl
6. Perl Poetry
7. Obfuscated code
8. Quests

For some of these, the prose can simply be grabbed from elsewhere, e.g. from (OBE) What section should I put this in? and from The Perl Monks Guide to the Monastery.