Good day,
While I very much agree with you (just look at my previous post in here) there needs to be a way to make entrance easier. 400 pages are quite a lot for those who rely on Whonix in journalism, etc.
What I feel is necessary to happen is that we take a very careful look at the current documentation and think about streamlining it. Your concept of different categories could be a part of the solution. Rewriting old text may be another one.
For the time being though, I need to find some way of replacing mediawiki without losing editability and without relying on JS. Am currently looking therfore into Jekyll as it is used by Qubes as well and seems to over the necessary features. Maybe using it for the homepage may be considerable though I need to look into all the scripts necessary to keep it running.
Have a nice day,
Ego