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I've never used SyncToy but any of these types of tools should work as the Kindle appears as a regular drive when it is plugged in. rsync is probably your best bet if you're not using a Windows OS.
The easy but basic option would be to just have a batch file or script which you run every time you plug the Kindle in. Somebody was trying to get it to work via the autorun facility in Windows but Windows won't allow you to have autorun files on a "hard disk" like the Kindle appears as unless you alter system settings.
jbcohen just can't keep away from the Kindle board for some reason. I don't I've ever seen a positive post from him regarding the Kindle.
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