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portal, rather than a a true "operating system" of sorts.

A standard Ubuntu install with nothing but a Firefox icon on the desktop
(and Flash/Java/Adblock-plus pre-installed for him) sounds like it would
be more than enough.

My mother was quite anti-tech for many years.  In the same fashion, I
started her off very simply.  The trick was to wait for her to ask for a
feature, and slowly introduce her to it (now she does all her finances,
photo editing, music editing and other things happily on her PC).
Bombarding anti-tech people with a desktop full of whiz-bang features
will only make them want to run for the hills.  Slowly, slowly.

-Dan