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because you can't move Kindle books like that. they are delivered to a device for use only on that specific device. so a book delivered to your actual kindle cannot be sideloaded to & read on your mac. Once again this is nothing to do with calibre though.
what you must do for your previously bought amazon books is install kindle for Mac, register it to your amazon account, download the books to your mac using that software. You can then place a copy of that in calibre, but that will not de-drm it unless you install extra plugins. calibre will by default call the amazon software as a viewer if you then open the book in calibre, so that will then work.
the mac copy is then licenced to be read on the mac, & only there, if you were to sideload THAT copy to a kindle it would be locked.
most foks who buy books + use calibre as their main library do de-drm after purchase, as that prevents all these new hardware-> new problems scenarios.
if you don't de-drm, you have no obvious way in calibre of knowing what device it is licenced for, unless you make custom columns. So wanting both the "licenced only for kindle" and the "licenced only for mac" copies both in calibre with same title, author etc will be confusing.
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