[Someone]

”and I'm still not sure it holds up in the real world“

Writing literature is a solo endeavour.

Modern programming is more like writing scientific literature, where multiple persons collaborate, and reading and understanding earlier work and maintaining a correct set of links to such works is half the work, if not more.

That, I think, is why literate programming doesn’t quite work. It works for Mathematica notebooks, iPython notebooks and the like, but not for larger works.