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I concur with pdurrant. Calibre makes life easier with the MAC from an organisational point of view, not just with the cybook. However you can just drag and drop.
wrt your last item, have a look at the mobi forum and read through the de-drm section. There are a number of hints and pdurrant has written a very nice applescript that will make life easy once you acquire the file.
To find the file though, do a google or equivalent for phrases like dark and reverser after reading the mobi de drm forum
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