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For my own part I simply wait until I have a suitable number of books, whatever that might be, before transferring over to my reader and tablet. That might mean it's a week since I last did so, or it could be two months. Then again for me having my entire library on the reader/tablet has nothing to with anything other than wanting to have it all available at all time. Primarily I guess that's because I never know what I might want to read next. It could as easily be a sci-fi or fantasy story as an old classic or a poetry collection, so I am "dependent" on having it all to hand.
Convenience or saving myself hassle really has nothing to do with anything in my case, since the work involved is so minuscule to begin with.
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