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I sideload all my Amazon books after cleaning up the metadata and DeDRMing. Data is synced, but I must do the following to update books:
I have a custom column called "#origfile" which is my send-to-device Kindle-specific template, containing the original filename that Amazon sent it to. This way, the calibre copy merely overwrites the copy that was on there already. And the sidecar {book-title}.sdr/ folder (matching the {book-title}.azw(3) file) containing the data will match up.
As long as the book was not converted, Amazon will recognize it as their book, and sync the data. This works just like the download-and-transfer-via-usb option on MYK.
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