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One thing that will help is if you avoid DRM products...not sure Calibre can convert or move a file if it's protected, so if your question is - can you share Kindle content from - say - Amazon that way...I don't think so. Not that I know of, anyway.
Welcome to the forum, though. You'll find plenty of books to share. Our CFO here at the office has downloaded a couple of my books to his Iphone, and he said it works very well.
David
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