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It would seem the problem is that calibre is not able to write to your Kindle's internal storage (the Read-only file system error). You might want to try using fsck.vfat to fix any errors on the partition.
Have you tried using a different USB cable? Or factory resetting your Kindle? Not sure where to find the reset on a Paperwhite 7th gen (on a PW 10th gen, it's under Settings => Device Options => Reset. Please note that this will require you to re-setup your Kindle.
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