Another thing that's been suggested over the years is a simplified calibre version, as the overwhelming number of various options turns off or discourages many potential users. Maybe instead of tackling the whole interface it would be easier to create a simpler version of the UI with fewer options and see how folks like that? If they do, some changes could then be gradually integrated to the main version.
Personally, calibre as it is suits me perfectly, but I've read many complaints about its complexity and UI, so I think there would be potential for "calibre-lite".
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