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As for reuploading the books to the reader, that depends on whether or not you've set your save to device- template to contain the authors field or not. You can find this in preferences->send to device, if the template contains {authors}, then the path the book ist stored in on the device depends on the value of the authors field, thus, if you changed that field, Calibre will not overwrite your files, but instead create another copy.
If you want to avoid having duplicates on your device, you might want to delete all books before resending. Keep in mind, though, that this may delete your reading progress, bookmarks et al. as well.
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