There is no way to cheat towards useful documentation. I think there are two rules:
Rule#1 - Please, in the name of all that is Holy, do *NOT* create a *^&@( Wiki. Write documentation. A Wiki is *NOT* documentation.
Rule#2 - Learn how to properly use M$-Office or OpenOffice. Seriously, this will make create and maintaining good and thorough documentation. In OpenOffice (sorry, don't know a darn thing about M$-Office) you can create a master document (ODM) that aggregates other documents and that will automatically create a table-of-contents, index, etc... if you use the styles correctly. It is *WONDERFUL* to use. And each section as its own file is much easier to maintain that one MASSIVE document and the auto-indexing makes it pretty easy to look stuff up (which also very much helps in keeping docs up to date). I have no doubt that M$-Office has the same features packaged somehow.
Documenting, especially creating documentation someone can actually use, is just plain hard work.