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Okay, a couple of suggestions.
First of all, I *never* use the Kobo Desktop software for anything if I can help it. To load my books onto my Kobo, I either use the Adobe Digital Editions software, Calibre software or download my purchased Kobo books via wifi--or a combination of the three.
I'd try using one of the above. Don't bother with the Desktop software at all. Let me know if I can help you some more.
I know it can be frustrating at times, but once you get things ironed out, it really is worth it.
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