I think we were on that trajectory until smartphones happened.
That might be true, but Windows, Mac OS, and even Linux desktops required far less technical skill to operate successfully in 2009 than in 1999.
If you tried to play games online in 1999 using Windows 98, it would break, and you would learn to fix it or you wouldn't play games anymore. Using Windows 7 in 2009, you'd probably have to know what compatibility mode is but it usually wouldn't break beyond that.
It is definitely smartphones. Any kid playing games on a PC would be forced to understand at least what programs are, what files and folders are, how to download games off the internet or install them from a CD, etc.
iPad kids just know "tap the square with the tiktok icon and swipe to make it go".
You don't need to know anything about files and folders to install and use Steam, which represents most of PC gaming and have done so for a very long time now.
People still learn those things to manually install mods and cheats, but it represents a fairly small subset of the overall gamer crowd. And if you look at the kinds of questions people ask on Steam forums that are related to that, it's clear that many users today have no concept of file system at all.
Lot's of kids still learn a lot from playing Minecraft Java-edition! There's a lot of skill involved in learning to setup a server, install mods, and it can't be installed through Steam, etc.
So its not entirely black-and-white, but I agree that for a large portion of people they do indeed never need to care.
Smartphones work very hard to obfuscate that files even exist, probably to push people to use cloud services. Hard to learn how they work if you can't even see them.
I needed to edit a file on an iPad. It took me a long time to find a text editor that could edit local files and wasn't a paid app.
I needed to edit something for a tether, IIRC.