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That's very generous of you. I hope that whoever you gift it to enjoys it!
I've been doing manual drag/drop for now. Here's a quick tip. When I setup my T1, I intentionally drag and dropped in small groups of books common to a collection. That way when you add them to the collection on the device they are grouped together already and you have to hunt less through pages of book listings to find them.
I use calibre for transferring books to my Kindle and Nook Color. I've been debating whether I should abandon the Sony software and just setup my entire library in calibre. Just haven't had time to deal with it. It's not that difficult to use calibre to create collections. Assign tags to your books using the names of the collections that you want.
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