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As far as I know Calibre does a match on the Title/Author combination. Therefore changing these in any way within Calibre will break the comparison with books already on the Kindle.
In terms of synching, there is no automated synching facility within Calibre. It is up to you to send changed books to the Kindle. You may find the Reading List plugin to be of use in the area of tracking what should be on the Kindle.
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