I believe you should have maximum of 3 levels of pages. So that you won't click away not knowing where you came from. You would rather have a few, very long, pages with this automatically generated table of contents.
Let's take Map Editing for an example. Either you'd want to know how to edit or you won't. If you do, you must now everything about it to understand and do it correct. You could have just one huge page with everything there is to know about editing. And before you even think about logging in to WME you should read that page, from top to bottom, at least once. You could have the basics (how to log in, which button to click, "and then save your work!"), when and where to use different road types, what to name them and why.
So take the Manual, BEP, How to label and name roads and Junction style guide and put them together at just one page.
Then you will know where to look to find your answer. Just go to the page about editing and find the right chapter in the table of contents.
One page about using the client.
One page about edit the map.
One page about "the rest".
But that's just my simple opinion...
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