I hate writing documentation.....
:)
Putting together some help file info for the new WinLib library I am writing and I find it so tedious. Wish I could make it more exciting. lol
I agree. I have the same feeling when I have to write manuals and documentation for my dayjob (mechanical engineering).
For software docs, probably the 'easiest' way is to add info to the documentation as you make progress with your software. If you add new functionality to the software, immediately add it in the documentation too. That way, the info is still fresh in your head. Doesn't have to be complete immediately though ....
There are some tools out there that help ease the pain a bit, mostly when it comes to document source code/libraries, i.e. Doxygen (http://www.stack.nl/~dimitri/doxygen/). Although initially aimed at C++, it can be customized for other languages.
As always when dealing with "niche BASICs", hunting down VB Classic or VB.NET examples.
Disclaimer: I haven't actually used it, but have seen a couple of help files created by it.