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I believe some of the difficulty lies in the fact it is cross platform, and needs to be relatively the same on Linux, Mac and Windows. Some more comes from the fact that calibre is a Swiss Army Knife and functions that are important to some are useless to others...ie. I would almost never use scissors on a knife, but need the screwdriver.
It also has to be maintainable and give no additional support headaches.
I hope you can succeed, because nobody is really happy with the current one, but it is hard to figure out how you can fix it without creating additional issues.
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