Yes, calibre can handle any number of devices as long as you don't connect more than one at a time.
Calibre doesn't really "sign up" devices. I suppose you mean you the setup wizard and selected one of these devices. Doing that really just sets a the maximum image for when you convert a book. You can always choose a different size when converting, but, I recommend just using the "tablet" option. This will mean the images are not resized and the device will do whatever is needed. For both the Glo and an iPad, this will work.
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