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emmgee, if you want to be able to add Kindle books to your Calibre library automatically on your Mac without Calibre deleting the files from your Kindle library, you can use an app such as Hazel to set up a script that automatically COPIES any new .azw files added to your Kindle library into a new folder (I've named mine Calibre Auto-Add), and then point Calibre to the new folder and tell it to automatically add any new files appearing there. So then all you need to do is open Kindle for Mac and download a new book, and it's automatically copied to the auto-add folder, whereupon it's added to your Calibre library the next time you open Calibre and then deleted from the auto-add folder. Does that solve your problem in a more elegant fashion?
Keep in mind that the first time you set this up, Hazel's going to move everything in your Kindle library into the auto-add folder. You can further restrict the script to prevent this, or you can simply let it do its thing and then empty the auto-add folder before opening Calibre. But after that first go, it'll run smoothly for any new additions.
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