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That's curious. I've sent recently nearly 1200 books to my Kindle 2 (just to see how much space they'd take up) and the process took less than 15 minutes over a USB2 connection. This, too, was on a a Mac -- a MacBook Pro running OS X 10.5.6.
Could the reason yours didn't work out be that your Mac went to sleep in the middle of the operation because there was no keyboard or mouse activity?
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