So as an experiment I tried to load a couple books to my original Kobo that had failed to load to my Kobo Touch. They loaded fine with processing time around 30 seconds or so. So it's obviously a problem specifically between the Kobo Touch and Calibre. I've now tried two different Kobo Touches, both of which experienced the exact same "Processing Content" freeze and failure of books to load so I'm guessing it probably isn't just an isolated buggy ereader.
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