@pirl8/ixtab: It's probably easier/neater to implement as a Calibre patch plugged into the conversion/preprocess stage than as a plugin.
Bonus hint: look at src/calibre/ebooks/hyphenate.py and enjoy not having to implement an hyphenation algo in Python
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I *might* take a look at it at some point, but it might be beyond my meager Python skills, so, if someone wants to jump in, be my guest
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Speaking of Calibre and hyphenation: Anyone managed to get the JS hyphenation working in the *viewer*, or is that just me?