In essence, all calibre does when sending a book to the device is to copy it there. Yes, it updates the metadata first, but after that, it is a simple file copy. So, yes, you can copy sideloaded books from the drive of one device to the drive of another. When you disconnect, the device will process the new books and add them to the internal database and hence the library.
But, don't copy the downloaded kepubs. These are added to the device and database in different ways. Copying the files for these books won't work.
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