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I have been using caliber for a little more than a week. When I first started using it, I too was disconcerted with the way it handled files. I almost stopped using it after one day, but once I played around in the GUI and was able to edit the metadata to have the books organized by Author/Series/Book Number, I began to see how Caliber really shines.
Like worldwalker said earlier. If you wanted to share a group of books (that are legally allowed to be shared), you can group them while in Caliber, then export them, in preparation to send to a friend. It is actually a lot easier than having to search through multiple directory trees.
The only thing you have to do in order to make this really easy is to edit the book information, I.E. the metadata when adding the book to your Caliber library, and all that takes is a couple of mouse clicks to have Caliber search online at the database that is like the IMDB for books. It is very easy.
As for your other two questions, they look to be specific to the 600 so I am not able to help with that.
In any event, I hope you enjoy your reader. Even with the things I wish Sony had done better, I really like my 505.
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