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You can move libraries over by just copying the library folder, opening it in calibre, and running the restore database option from "Library Maintenance". It will rebuild the database according to the unix structure of a Mac filesystem, and grab library settings from the json backup, too!
I think you will have to reinstall your plugins, but I know Alf can backup your keyfiles, or you can copy over the %calibreconfig%\plugins\dedrm.json as it appears to be fully platform-independent. In fact, you can probably copy over the whole plugin folder, but you may need to install each plugin again anyway so calibre notices the addition -- it is recorded in another file somewhere.
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