Many years ago I worked as a copy editor. For a while I imagined, as many copy editors did, that my task was to enforce the rules of the University of Chicago's Manual of Style, especially regarding placement of punctuation with respect to quotation marks, "which" v. "that", etc. Eventually, I understood that making such changes was useful, but not really what editing should be about. It is possible to have unreadable or awkward prose with perfect comma placement, semicolon discipline, and no "which"es without a comma before them.

I doubt that I was or am nearly as good an editor as he is a coder. Yet I think that there is a logical progression (not a natural progression, since we don't all make it) from knowing the rules to knowing what the rules are for, to having the confidence to break them when it makes sense.