I have checked some other projects (django, tg, pylons, python.org
etc). My understanding is that,

=> The core documentation must be maintained by core-devs who know the
code inside out, This doc is the ultimate reference and should be in
Restructured format text-files, in  a SVN/Hg repository.

RST to HTML conversion should be performed and published online. Users
should be able to submit comments (Django allows at the paragraph
level, pylons allows comments at the page level). These comments
should be reviewed the core-dev or core-doc team and the docs updated
frequently.

=> User generated docs which are likely to contain errors ,
inaccuracies, tips, hints etc should be maintained in a separate wiki/
site such as moinmoin or a CMS such as Drupal or Joomla. Some
extremely useful tips etc can be pulled into the core-docs. Some can
be left in this state and maintained separately.

I am accumulating all my comments here: 
http://webtopy.org/community/w2py-doc-conundrum

I am willing to assist in a one time Latex or PDF to ReST  manual
conversion . A group of members on this list can form a taskforce and
splitup chapters and perform the conversion.

If one of the list members can come up with a budget and a deadline to
develop a kickass web2py wiki, we can come up with contributions /
funds. I am willing to put up USD 100

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