Okay, so I checked the Dropbox system tray and when I read and bookmarked a book, it changed the epub itself as well as iterator.pickle and viewer.json.
Exited calibre, made sure Dropbox was done syncing on PC 1, fired up PC 2, made sure Dropbox finished syncing on PC 2, fired up Calibre, opened the last book I was reading and the bookmark and last read location was all correct.
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