If you are reading kepubs from Kobio, sync the Touch to the server before setting up the Glo. When the Glo is setup, it will automatically download the books and bookmarks.
There isn't a way to do this completely for sideloaded books. A copy of the bookmarks for epubs are stored in files under "Digital Editions/Annotations". You can copy these files over to the Glo. As long as the epubs are sideloaded to the same place and with the same name, these will be read and loaded into the database when you open the book.
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