if it looks empty in windows explorer, then there is something wrong, outside of calibre.
either you have the wrong driver or windows is seeing it as a media player, not as a storage device. for the latter, there may be a toggle inside of kindle settings that you need rot find and flip, then re-connect it. if you have the mayday feature, then you may be able to get amazon to fix it for you .
if not you may have to try various permutations of connect via usb when kindle is off off, or when on + awake, or on + asleep... until windows sees " new hardware" & decides to install a driver. windows + USN + KF do not always play nicely together.
But once windows can see the storage ok , calibre shoudl also be able to.
Your other option is to skip all that & do everything wirelessly via the calibre companion app, which is in amazon store.
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