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"Is there some way to measure whether our own application of rule-breaking is done well?" Yes, that tool is called readers. Give your writing to a number of critical readers and see what they say.
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#3: Attribution notice added
Source: https://writers.stackexchange.com/a/43528 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/