> Answering that question is the very reason for pausing to investigate its purpose.
So you answer the question and determine the fence is there because of adverse possession. And then everyone else you present your findings to says, "that's not a good reason, so clearly you're not using Chesterton's fence and we shouldn't make any changes." See the issue?
Chesterton's fence and/or the Principle of Charity only have the potential to lead you to a good answer if the other party is putting in a good faith effort. But as soon as that's not the case, these cognitive rules of thumb basically become tools of oppression. And if you've ever watched congressional testimony where the parties are forbidden by rule from criticizing each other, it's easy to see that lots of people purposely take advantage of this.
Also, in the context of business the PoC means assuming that people are acting in their self interest, but in the context of politics or whatever it means assuming that people aren't acting in their self interest. As a rule of thumb for improving your thinking then these sorts of ideas probably make sense, especially for things like entrepreneurship or software engineering, but at an epistemological level the phrase "not even wrong" comes to mind.