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What I did with my mother when she had a Sony Reader was to put all of her eBooks on it for it. using a combination of Teamviewer and Skype. I would run calibre, send all the books to her laptop, import them into calibre, then I'd have her plug int he Sony, press the button on the screen to connect. Then I would send all of the eBooks to her Sony. I would delete any of the eBooks she had finished reading. Then I would eject and she would unplug and be good to go.
It meant I did not have to drive over to her place just to add some new eBooks to her Sony. I could also help her from home if she had a computer problem. It was a really good solution.
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