Any pointers on how to make it easier to wtfm?
If anyone out there actually enjoys writing documentation I'd be willing to pay for some help and guidance on a rather large commercial open source project that is in need of some tlc regarding documentation
In the Python world, readthedocs.org has made writing docs easier - it takes care of rebuilding documentation each time you commit. It's implemented in Python, and most popular with the Python community, but it can be used for other languages as well.
API documentation can be generated from the source code with tools like doxygen. For everything else there's the standard toolchain consisting of a good editor and source control. Writing documentation is a chore but it's a very important aspect nevertheless.