Some ebooks are fixed layout or other aspects that don't work on Kindle eink. If you can't buy a book it's incompatible. The CS person was wrong to make you re-register.
Make sure you have DeDRM from NoDRM Git and copy / paste serial number from My Content & Devices to the Plugin.
Delete all visible ebooks & associated files of different ending using filemanager of any kind via USB. Do File Check on the Kindle "drive".
Go My Content & Devices on Amazon and download each ebook for that Kindle.
Only ever transfer ebooks FROM Calibre to Kindle. If there is DRM stuff is broken with a different Kindle and re-registering may look like a different Kindle.
Add them to Calibre.
Transfer by Send to Device.
If you skip the de-drm step you can only transfer books since re-registered. The previously downloaded ones may have wrong DRM code.
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