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I generally update under one of three conditions ...
1) The apparently most common theme of 'Whenever there's a feature I like/will use' with the added application of if a plugin i use is updated beyond my current level.
2) Every 5 updates or so - so I just updated to .55.
3) Whenever I'm trying to teach someone Calibre, since they're gonna have the latest version, I update as well so I'm not baffled in case they ask about new features.
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