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with Dropbox and Calibre you won't have any problems - you can also use OPDS to create a catalogue and browse the online catalogue you created (which is easier to organize as you wish) rahter then your Calibre library (which I have online just in case as a backup anyway). That said, this would be more of a need if you get a reader with no expansion for a card. In my case, with a 8GB additional micro card, I prefer to carry all my books with me. But some people don't like the way the reader software organises their books, in which case it may make sense not to hold a long list. As benham said, once you have pinned down your shortlist of readers, you can then study better the details for each particular device. But what you propose is certainly doable with several readers!
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