I've only skimmed this thread so I apologize if I miss something but I
was thinking. Might it be a better idea to make the user at least
somewhat responsible for the backup?

I was thinking you could use a program like Tucan[1] to get them to
sync their portable data to a specific volume on the network and then
just use BackupPC to backup that volume.

Of course this relies on the user to take some action but I think it
would take a lot of complexity out of the solution.

Richard

[1] http://portableapps.com/apps/utilities/toucan

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