One annoying problem with "Features in Depth" on the Documentation page  is that once you click on say "Editing" that page is actually missing the last subtopic "Code Formatting" (presumably because that is a v2 alpha only
feature). Similarly the "Projects" page is missing the "Virtual Env" subtopic.
I suggest you somehow highlight those two pages on the main Documentation page to indicate that they need to be clicked separately (or just add them to the end of their respective topics).
Another, annoying aspect is that there is no way to navigate to the "Next" topic. You have to return to main documentation page and figure out yourself what the next topic (or subtopic) is.
Of course, what I really want is a separate Contents pane on the left (with the current page indicated somehow) but I presume that isn't possible with this wiki system? In addition, the wiki doesn't seem to have an "all pages" page?
I find that wikis aren't really all that great for documentation that is meant to be read like a book (or article). Instead may I suggest you just convert these pages to Sphinx and publish them on readthedocs.org? I'd even volunteer to do the initial conversion
(which shouldn't take all that long).
BTW, the IronPython page on Python Tools  prominently refers to a Walkthrough . This page is currently unreachable via the Documentation page (presumably because it has been superceded by the "Feature in Depth" links).