There he talks about rules that matter, and rules that don't, and I think that partially encompasses my attitude.
But only partially. In addition I'd add: when it makes things better.
When people break the rules here they usually make things worse. Duplicated items split discussion. Multiple items about the same story with no extra information dilute the "New" and "Front" pages. People who leave witty replies that teach us nothing reduce the information density.
I expect there are ways of "breakingthe rules" here on HN that make things better. Generally people frown on "meta" items and discussion. I break the "rules" on that, so do others, and sometimes we get down-voted, and sometimes not.
It depends.
Does it make things better? That's my usual guideline, and that's why I've taken the time to reply to you, even though your question could be taken as a content and information free jibe. Maybe it wasn't intended that way, so I'll assume you were intending to be helpful, and provide my thoughts for your consideration.
The reason I asked was because a while ago you had posted about flagging people who you saw as breaking the rules, and I was wondering how you reconciled that with your very valid point here that the only way to keep a community vibrant is to break the rules. Your answer here makes sense and is pretty much how I think of it; for example, I knowingly break the rule of "don't bring it up if you're downvoted" knowing that my popularity will take a small hit.
The challenge though is that what rules "matter" and "better/worse" are subjective -- and when groupthink sets in, attempts to change the rules are opposed even if many people think they would result in a better community.