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Gregg Bell - you could get something like a refurbished HP Mini (because its small) with a kosher Windows 7 licence to do your DRMing etc. Here's a guide to sharing files between Linux and Windows ==>>
How to Share Files Between Windows and Linux. And of course there's always the pain free sneakernet option.
Down here a refurbished HP-Mini can be had for ~AU$100, I would think a lot fewer US$'s over there. Yes, I am aware of your problems with a refurbished Sony Reader.
In essence I agree with JSWolf's sentiments in post #6.
Kovid Goyal makes some interesting observations in which you might be interested ==>>
Linux definitely has more problems than any other OS...
Quote:
As it is now, I have no idea how a non-technical person is ever going to maintain a stable and fully functional linux system.
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BR