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I think centralization played a big role in this, at least for software. When messaging meant IRC, AIM, Yahoo, MSN, Xfire, Ventrilo, TeamSpeak, or any number of PHP forums, you had to be able to pick up new software quickly and conceptualized the thing it's doing separate from the application it's accomplished with. When they all needed to be installed from different places in different ways you conceptualize the file system and what an executable is to an extent. When every game needs a bit of debugging to get working and a bit of savvy to know when certain computer parts are incompatible, you need a bit of knowledge to do the thing you want to do.

That said, fewer people did it. I was in highschool when Facebook took off, and the number of people who went from never online to perpetually online skyrocketed.

I teach computer science, I know it isn't wholly generational, but I've watched the decline over the past decade for the basics. Highschool students were raised on Chromebooks and tablets/phones and a homogenous software scene. Concepts like files, installations, computer components, local storage, compression, settings, keyboard proficiency, toolbars, context menus - these are all barriers for incoming students.

The big difference, I think, is that way more people (nearly everyone) has some technical proficiency, whereas before it was considered a popular enough hobby but most people were completely inept, but most of students nowadays are not proficient with things past a cursory level. That said, the ones who are technically inclined are extremely technically inclined compared to my era, in larger numbers at least.

Higher minimum and maximum thresholds, but maybe lower on average.