in reply to offline html help generation
What your quest basically comes down to is separation of data and presentation. Both Mason and TT2 (and all the others) are capable of making this possible (offline/online/whatever).
At the moment I would lean towards http://tt2.org/download/Template-Skeleton-0.01.tar.gz (the driving force behind http://tt2.org/tt3/, http://wardley.org) as an amazingly easy to grow starting point (see the oscon2003 "tutorial" above). Grab yourself an INSERT directive and you've got data you're maintaining in one place automagically inserted wherever you need it.
I would also suggest a Wiki (such as http://kwiki.org/, CGI::Wiki::Simple...) as means of user contributed documentation.
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