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The thumbnails are indeed B&W renditions of the covers and are very compressed (to save space, most probably). Obviously, with a large book collection, this could take a while to redo. I had 90 books to do. I ended up resizing them to the same resolution too (142x217) to make a coherent display (ie, no large thumbnails next to a thin one, etc...). Yes, I am a freak :P
As for Calibre doing it automatically, I don't see how. I made a test ; I sent the thumbnail using the proper file hierarchy in the thumbnails folder right after I sent an eBook (that folder had to be created, as the Sony Reader will only do so after you disconnect it from the computer) and the Reader ended up creating its own anyway. So I had to re-connect and save that new thumbnail again.
Which means that even if Calibre were to send thumbnails alongside the eBooks using the proper structure, the Reader would still re-create them when disconnected.
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