Thank you a fun read, Mr. Miller!The title suggested something dystopian or numbingly bureaucratic to me, and glad it wasn't. Following is an additional thought about the language evolving.
Broadly, language evolves because of how people use it. So as you discuss, guardians of the rules rightly change the rules to reflect language's evolution.
This implies a shifting gray area between breaking the rules and following the rules -- one day it's a violation, the next day it's proper style.
At any given time, violations are being made that will never become style -- at least not in our lifetimes. So arguably, we shouldn't break the rules willy-nilly.
When one has been reading and writing a lot -- perhaps for many years -- and trying to (or being pressured to) follow style, I see a judicious approach.
I write a sentence in good style. I then read it back. If it sounds too odd or doesn't communicate well, I change it to something that mildly breaks the rules, yet still sounds fairly proper to a literate reader. I see this as moving in concert with evolution.
In other words, I've read here and there that to legitimately break the rules, you first have to learn them. In effect, really good writers (I'm not) in their writing show us how the language should evolve.
This process is reflected well in the history of music, by the Beatles most notably in our time, and other arts.