My method is using the Reading List plugin.
For each of my ereaders, I have a send-on-connect reading list. For a new device, I would first create the reading list. Then I would connect the old device, select all the books on it and add them to the reading list for the new device. Then when I connect the new device, all the books are automatically sent to it.
I keep the reading lists for later syncing. For a new book, I decide which devices I want the book on and add it to the appropriate reading list. When I connect the device, the books are automatically sent.
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