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From my perspective, the issue is not that you would both have all the books (after all, there is lots of room), but rather, the sync function if you both are reading the same book at the same time. I would not set up separate accounts--just in case you do want to read the same books without buying them twice.
Try sideloading loading via Calibre again. It really seems to work for most people. Be sure you have the most recent version, and be aware that the newly improved Kobo Calibre driver is scheduled for the next update--through this one seems to work pretty well.
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