Eli, I imagine that it is more complicated than just turning attention to the user. I am not a programmer. I have not done any technical training. All my knowledge is self-taught. I may not know what all the errors mean, but I can at least debug to a degree. My actually occupation is the delivery of a sector-wide LMS. I am a teacher whose job it is to make connections between the technical and the pedagogical. My experience is that this comes down to storytelling.
I feel that what is needed are more people in-between the divide of Gen 1 & 2 vs. 3 & 4. People who are living it, asking questions and identifying the various points of confusion. I think this is what will take the #IndieWeb from a hipster-web to a “demonstratably better web“