I have two kobos one account
My wife and I each have a Kobo (1rst Gens) and share one account. We've been doing it since August and wouldn't consider anything else. Our reading preferences are quite different but occasionally overlap.
Sideloaded books without DRM are simple because I either just drag and drop or use Calibre. Books from Kobo with DRM I usually upload to one Kobo with ADE and the other with the desktop (one of us preferes a cover to all the books the other doesn't care). All in all very simple.
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