After playing around with epydoc and a epydoc-to-chm conversion script for my own projects (and getting acceptable results) I tried the same without any further preperation for the Pylons 0.9.6.1 / Webhelpers 0.3.2 versions I currently use.
I also did a try with paste but the resulting file was above 2 MB so I didn't want to flood the people here 
See the result attached - not as good as my own doc's, but Pylons/Webhelpers is probably not that epydoc focused as my own source. Some things are missing (I'm also getting errors while compiling the chm file - missing links). Would need some further investigation why... I even had a epydoc crash for the webhelpers parts which needed some quick fixing at the epydoc source.
I don't know how many of you are Windows focused. What I find good with the chm files is the full text index and the full text search capability. There are linux viewers avaiable, so maybe even the Linux based developers would find this good.
Is there any interest for those chm files?
I could make a optimized Pylons+Paste+Webhelpers combination if people show interest.
Great job. I'd like to see the further work on this.