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Which firmware version is the Glo running? Are you sideloading ePubs or KePubs?
The Glo has never needed the cover image to have any special name in ePubs, but I don't know about kePubs. Perhaps Calibre itself might use the filename to decide which to use as cover if it can't work it out another way though.
If signing out worked then it would wipe the database and you would lose all your stats for sideloaded books anyway. A factory reset also reformats the filesystem and so you also lose the sideloaded books themselves and have to reload them, but that should not be much trouble if they are all in Calibre.
I don't know what could cause signing out to fail, the only possibility that comes to mind is if you are running firmware 3.16.10 or 3.17.0 then the over-zealous sickel process might cause the device to reboot if the sign-out procedure was taking too long.
You might want to wait to hear from davidfor or someone with ideas about what you could do to recover the reading stats of sideloaded books from the database. But I don't think it is a simple process unless you already have a recent backup of the database from before it was corrupted.
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