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Hmm... I like the Dropbox idea although I haven't really got an idea of how Dropbox works itself (might be useful beyond books).
I tend to have more books rather than less and use Calibre to set up my collections. I have found that things slow down when I get up over 100 books. I'm not sure it is a specific book because I've also had indexing problems and can usually find those quickly.
I do find having a lot of books frustrating from a browsing point of view. I have about one to two pages of collections including a currently reading one, but I like to sort them by title as it keeps it orderly for me. This of course gets a bit crazy when there are many books on the device. It's not horrible as I usually limit myself to the first couple of pages of collections (special characters keep those at the front), but it still could be better.
Something like Dropbox may be good for cutting myself down to very few books, but I'll have to see how flexible that service is.
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