Earlier quoted context omitted.
It's been a while since I dumped OSX and went back to Linux, but IIRC, this setting gets reset every time the system updates. At some point Apple realized the "power user" market was too small, and they were better off treating all of their users like idiots. And that's when I left.
The power user market was never that big for Apple since Mac Classic came to be, that was the target market, the "idiots". Desktop power users were on the Acorn, Amiga, Atari and PC. As NeXT "acquired" Apple, Linux users thought OS X was the UNIX experience they were looking for, and since they were never part of Apple culture, keep getting their expectations wrong.
They never set out to build the ultimate power user machine, their target was still general consumers. They just happened to have the right product at the right time when everything else just failed to compete.
Had desktop linux been in a better state, or had MS built WSL earlier, things might look a lot different today.