> ...I go back in git history to when the config was introduced to understand why it was done the way it was, in case I am missing something. I call this "paying the Chesterton Tax.

Maintaining code I wrote 15-20 years ago I find myself doing this with my own commits. I have to get back into the mental place I was when I wrote the original code and then it usually becomes clear if it was an expedient hack or a thought-out solution for a corner case.

The worst feeling is "cleaning up" some code, discovering the edge case under which the "simple" case fails, then re-implementing the same solution.