My wife and I started talking about this after she had to help an old lady at the DMV figure out how to use her iPhone to scan a QR code. We're in our early 40s.
I'm of a similar age to you. In my elementary school, we had to learn to use Windows 95, Apple II PCs, iMac G3s running OSX, Windows 98, and I think we had to type a few DOS commands in for e.g. playing Oregon Trail on floppy disk.
Before us were people who mainly learned computers as command prompts, after us were kids who got OS X as their idea of "a complicated computer".
To me OS X felt like playing with those oversized Duplo blocks when I was used to regular Legos, y'know? Too simplified sometimes, but you could make it work.
Nowadays people barely know what files are, let alone the dark arts of CLI.
It's a weird feeling, having seen technology explode in complexity, then implode into crippling oversimplification. Not like simple tech didn't exist before, like game consoles, but now it's all average people understand.