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Completely inadvertantly, I seem to have done this. I didn't think it was possible, but I downloaded a book and converted it using Calibre, then sideloaded it to my (wife's) K2. About a week later I sideloaded it to my Fire. When I started reading it a few days later I got the popup asking me if I wanted to sync to the furthest location (which is where my wife had read to).
I think that's bow it all worked, anyway. So it is possible.
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