I don't have answers to all the questions posed, but I have been
trying k9 (http://www.k9webprotection.com/) as a web filter on our
home windows machine and it seems to work well.  It is made by the
same company that provides Bluecoat to enterprises.  It's not OSS but
it is free and easy to use.  I would be comforable recommending it to
non-techies.
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