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I would suggest you plug in the device while Calibre is running. Click on the heading which shows the green check indicating books that are in the device. This will bring them all together at the top of the list. Then Select those items and "edit metadata" to add a unique tag to them; make it really unusual like "ondevice4transfer" or something like that. Essentially now you are done, as you can recall those books from your collection at any time.
When you get a new device, just plug it in and search for that tag and copy those books to the new device.
If you want to clean up after yourself, which is optional, just delete that tag from those books.
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