2. Big/Ugly projects we avoid. I've noticed that one of the worst usability issues for wp.org is Media—inserting a picture is still a painful. Why hasn't it been fixed? In part, because it's a messy coding/architecture problem (so I've heard) and no one really wants to take it on. We have similar stories in Automattic (the Store has a similar rep for being a bear to work on). And important things can be broken for weeks or months when they fall off the radar (e.g. LinkedIn Plugin). I'm all for incrementalism but some projects are harder to take on this way. I bet every team has a pile of
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