Recently I was helping someone in my life who'd gone through a stroke (not too old or tech-unsavvy) to learn a password manager and go through various websites' password reset flows. It really forced me to confront the reality of what you described, i.e. that computing really has become an inscrutable, confusing mess where nothing makes sense and we've just come to accept it.

It used to feel like being "tech savvy" meant thinking logically as the system designers would have, but now I think it just means being conditioned through years of abuse into knowing the unwritten rules of how to skillfully outmaneuver bullshit interfaces and dark patterns.