So... one of his key problems is that when (not if) things break, you need to learn more than you ever wanted to know about the low-level internals of an OS to fix it. And you say you've never had that had that problem; you should have a deep understanding of each component and the system as a whole in order to be able to use Linux.
But that's exactly one of the major problems he's complaining about!
It's a different philosophy. Some of us come at it from the perspective that we want to know how our machine works. And when something goes wrong, we want to dig into it and fix it ourselves. The monolithic and opaque OSs that "just work" aren't for us. Oddly, the only place I've seen this attitude described/explained is in Zen and the Art of Motorcycle Maintenance.
But that's exactly one of the major problems he's complaining about!