What language and/or system were you writing in? I discovered literate programming in 2003 and was excited by it (still am). But it never took off and the tooling was poor (Leo, the Literate Programming Editor, is the one I remember - and shudder thinking about)
https://news.ycombinator.com/item?id=12398098
I'm still on that "detour," but still a believer.
Edit: some dead links there. This "bootstrap" directory contains the custom tangler and the custom rule processor. This 10K, plus the tiny configs in the root, are the only code in the project not in documents.
https://bitbucket.org/gavinpc/willshake/src/master/bootstrap...