There was a post here a while back about how younger generations often don't understand concepts like file system structures because concepts like that (which are still relevant in a lot of contexts) have been largely stripped out of modern user interfaces. If your primary computing device is a cell phone, a task like "make a nested directory structure and move this file to the deepest part of it" is a foreign concept.

I guess my point here is that I agree with yours about this being cyclical in a sense. I feel crippled on a cell phone, but I'm also in my comfort zone on a Linux terminal. Using web apps like MS Teams is often difficult for me because their UIs are not things I'm comfortable with. I don't tend to like default layouts and also tend to use advanced features which are usually hidden away behind a few menus. Tools built to meet my needs specifically would largely not meet the needs of most users. A Level 1 user would probably have a better experience there than a Level 3 like me. It's hard (maybe impossible) to do UX design that satisfies everyone.

I have a large chunk of my colleagues who have little to no experience using CLI tools, and totally have found the last part to be true. In fairness, documentation is all over the place quality wise (I generally find Microsoft's useful but I've totally had issues in the past with undocumented or vaguely documented features/dependencies). People will google their issues, and increasingly I've found it doesnt point you at the documentation directly, instead stack overflow or medium pages.

I feel like there's definitely some conceptual... Stuff for lack of a better word that's an issue, I've seen a number of people focus on the execution instead of trying to understand what's the issue and define it logically, when pressed they struggle to explain.