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Why not just email the books to your Amazon cloud using send to Kindle,
Then you can download them from cloud to Kindle as needed.
No need for cc or for the intermediate devices. All you need is that external hd attached to something that can send emails,and attach one book to each email. Yes you have to do them one at a time but you can only read one book at a time anyway
Copying the books to other cloud solutions e.g. dropbox then getting them via the Kindle browser is another option
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