[cybmole]

you need to register the new device to the same amazon account that you used for old device / old book purchases.

once a device is linked to an account it should be able to access all books bought using that account, however they are loaded i.e. it should not matter if calibre was used for interim storage. a purchased book is linked to a specific amazon account. that link should stay within the book file if added to vanilla calibre without any de-drm plug-ins. Calibre just files a copy of the .mobi or azw file without altering it.

so anything that worked on your old paper white should also work on your new paperwhite

it used to be the case that a new Kindle would arrive unregistered & you had to explicitly register it. dunno if that is how it still works. check your registrations