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@maraxion-
Unless you have Calibre setup to convert on sending to device, yes you need to reconvert after changing metadata and covers for them to stick (at least for covers). Also, the cover size needs to be appropriate -- PW's are touchy about this. I've found the easiest thing for me is to use the Resize Cover plugin for Calibre (you can pick which size you want...I just use the default and it works fine).
If you can read the book, then the format to send option is okay.
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