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your requirements contradict themselves.
you want to be part way through a book on Kindle, but i you also want to be able to change the version of that book that's in the calibre library, have the new version sent to Kindle, & somehow magically have the software know where you reading position is within the changed book ?
a bookmark or a lest page read relates to a specific instance of a specific book- you can't change the book without sacrificing the bookmarks
it is asking for trouble to send an altered version of a book to a device, without first removing the previous version from the device.
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