We just finished up out project and now its clean up time. Now its time to document some of our tools.
How do you deal with documentation?
When I do document (I am bad about it), I’ll use video tutorials. It helps new users to see the tools in action.
I usually break it down to technical documentation and written/video tutorials.
With the technical documentation I lay out in detail what makes the tool work, special requirements it might have, and any quirks that might be in the current version.
With the tutorials I find it is very important to at least have a very simple step-by-step instructions page that anyone can go through within a few minutes. People don’t like to read apparently. 
Videos are great for a quick overview of how a tool works. It’s a pain to have to read through a page or more of text when you just want to see what something does. But you need to back it up with a help page for the people that already know how it works, but need a refresher on one specific element. It’s also a pain to have to watch of few minutes of video when you just need one small piece of information.
Of course, I don’t do either very often. :): But we’re currently refactoring many of our tools and I’m implementing a system that should make it easier to maintain the help files; easier for me to make, and easier for the users to find and use.