Yeah, I think one of the issues is that a knowledge gap is a very hard thing to bridge. Part of that is the classic thing that “we don’t know how much we don’t know”. But there’s a similar thing with knowledge, where people don’t know how much they know.
Like with the terminal, once you get comfortable with it, it is really easy to get things done, but you really have to have a certain kind of disposition to get to that point, even with the right kind of help - like with your dad, if he’s not interested to learn you can’t make him. You have to already be deep into the ecosystem before you can say “it’s easy”, and by that point you are so far removed from the average user’s experience that you can’t understand why they can’t just do what you do. And unfortunately, the people most expert at using linux and therefore developing it are also the people deepest in the ecosystem.
There’s an empathy gap that’s hard to bridge, but it’s not impossible. Like if you’ve ever finished The Outer Wilds, it’s an incredible game that is only gated by your knowledge. It’s a unique experience that you can’t repeat. The only way to attempt to experience it again is to sit down and watch another person’s playthrough of it. I’ve done it multiple times, and each time is a unique and difficult experience, because you already know the answers, and they are so painfully simple once you know them. It’s a real struggle of empathy to actually be able to enjoy it.
You can do a similar thing with other freeform puzzle games like The Witness. It’s just that The Outer Wilds is unique in that it shows you in stark contrast how vast the gap is between knowing and not knowing, and you have to bridge that gap constantly in order to engage.
So that’s my ramble on that subject, but that’s what I think is happening. I think apart from people willing and able to bridge that gap, the solutions to this issue involve more resources dedicated to improving the ecosystem and making it friendlier, and also just more uptake making the system stronger and exposing its weak points as people learn it, making the empathy gap less of a problem. As we are, proprietary systems have sucked up all those resources and market share, which has starved open source. It’s a slow climb out of that hole but I have to believe that eventually there will be a critical tipping point.