This is something that's been on my mind a lot over the past few years. I think things were on that trajectory, but somewhere along the line it got out of wack.
User interfaces became more user-friendly [0], while developer experience - though simpler in many ways - also became more complex, to handle the complex demands of modern software while maintaining a smooth user experience. In isolation both of these things make sense. But taken together, it means that instead of developer and user experience converging into a middle place where tools are a bit easier to learn and interfaces a bit more involved, they've diverged further, to where all the cognitive load is placed on the development side and the user expects an entirely frictionless experience.
Specialization is at the core of our big interconnected society, so it's not a surprising outcome if you look at the past century or two of civilization. But at the same time I think there's something lost when roles become too segregated. In the same way homesteading has its own niche popularity, I believe there's a latent demand for digital homesteading too; we see its fringes in the slow rise of things like Neocities, the indie web, and open source software over the past few years.
Personally I think we just have yet to see the 'killer app' for digital homesteading, some sort of central pillar or set of principles to grow around. The (small) web is the closest we have at the moment, but it carries a lot of technical baggage with it, too much to be able to walk the fine line needed between approachability and flexibility.
Anyway, that's enough rambling for now. I'll save the rest for a blog post.
[0] user-friendly as in being able to use it without learning anything first; not that that's necessarily in the user's best interest