I always update macOS, iOS, tvOS, whenever a security update is available, and my three Linux servers on a weekly basis. I have never had an update go wrong. To me (and many security professionals), convenience is the enemy of security.
But of course, you know what I do for a living. So maybe my advice to always, always, perform the security update for personal devices will be ignored. Fifteen years of experience and knowledge will count for nothing with people like Stephen Pieper.
I’ve got a wife and kids and elderly parents and elderly parents-in-law. I’ve got people to protect.
To quote David Halberstam writing about political leaders,
They were brilliant and they were fools.