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If you've got a Sony there is an option that's a bit simpler, though it doesn't solve things 100%.
You can go to:
Preferences -> Advanced -> Plugins ->
Device Interface Plugins -> SONY Device Interface.
Check 'Upload separate cover thumbnails for books'
Check 'Refresh separate covers when using automatic management' (only if auto management is enabled, and this is optional.
Choose your preference on cover aspect ratio.
If you want the covers to always be updated automatically (even after changing them), make sure the second option above is enabled, and also go to Preferences -> Sending to Devices, and enable Automatic management.
This will give you Calibre's thumbnails for all your books in the book browsing view on the Sony. When you actually read the book you'll get whatever the actual cover on the ePub is.
There is also a small quirk with the Sony devices where you can lose the Calibre cover the first time you load the book onto the Sony, but the automatic management option I mentioned will fix this during subsequent syncs.
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