I can confirm the missing cover issue, at least for some books.
I looked though my oldest Kindle book purchases on the Manage Your Content and Devices page and quickly found one purchased in 2012 with a "No image available" cover shown. Clicking the title goes to a "page not found" dog photo, indicating that the book is no longer available for sale on Amazon.
Trying to use Download and Transfer on it results in a "Something went wrong" error popup.
I am able to use "Deliver or remove from device" and the resulting book shows on the device with a generic cover image in the library view.
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