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I'll toss out a couple of basic questions:
Are you going to have your Calibre library on the PC, the Mac, or are you both going to run your own instances of Calibre with your own libraries and share books manually?
If you've bought books and they're DRMed, Calibre won't be able to convert them. Does that kill your dreams, or do you have mostly non-DRMed books?
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