Doesn't this contradict the popular wisdom that "what's good for a human engineer is good for an LLM"? e.g. documentation, separation of concerns, organized files, DRY.

I find LLMs very useful and capable, but in my experience they definitely perform worse when things are unorganized. Maintenance isn't just aesthetics, it's a direct input to correctness.

Maybe a little. I don't hold fast to that popular wisdom, e.g. I think comments are not always a net positive for LLMs. With respect to technical debt, how much debt is too much debt before it gums up the works and arrests forward progress on the software? It probably depends on the individual programmer. LLMs do seem to have a higher tolerance for technical debt than myself personally at least.