I don't think we're making progress at all. My theory is that software is made simple enough for a typical 20's-ish person who's already familiar with that kind

I don't think we're making progress at all. My theory is that software is made simple enough for a typical 20's-ish person who's already familiar with that kind of thing. But less capable people are still left out just as they were in the 80's, 90's, 00's, etc. In the 90's, it was hard to figure out how to connect a VCR to a TV. Today, it's hard to figure out how to connect a Chromecast to a phone. The mental difficulty is not less at all.