Some time back I blogged about the Sandcastle project over at Microsoft, a tool that allows you to generate MSDN-style documentation from the comments in the .NET code (among other things). I recently downloaded the Sandcastle - June 2007 Community Technology Preview (CTP) to generate some documentation for a project we did with the HPC team at Microsoft. Even though it is still a CTP, it works great – right now I am able to add comments to the code and then generate sufficient documentation semi-automatically, killing two birds with one stone.
If you are interested in using this tools, make sure to check out post Creating a Chm build using Sandcastle at the Sandcastle blog . Remember that Sandcastle will extract and transform the comments from your files, but you still need the HTML Help Workshop to create the actual *.chm file.