The most common explanation I’ve seen, and imo it makes sense, is that things mostly just work now. Even XP required a helluva lot more troubleshooting and messing with stuff to make it work than today. So you not only have a bunch of people that have no troubleshooting experience, a large portion don’t even know how to properly search for things.
On the flip side, you have a lot more people doing insanely impressive stuff at a lot younger ages because if you have the drive to do it, there’s more material to learn than ever out there.
I’m sure this varies a lot from district to district, but the districts that I have teacher friends in, they’ve been using Chromebooks almost exclusively for the better part of a decade now