Using Python to generate CHM and Word manuals
pydocgen is a Python-Powered script to generate Microsoft Word (TM) documents and HTMLHelp files from a plain HTML source.
As an example, this HTML source was used to generate this HTMLHelp file and this Word document. Incidentally, these files are the documentation for pydocgen ;)
You can download the required files here.
Generating docs for the Python Standard Library
There is a special version of pydocgen that generates a helpfile from the docstrings of the Python Standard Library.
You can download both the sourcecode and the helpfile.