True. The History as a First-class Citizen - #61 by khinsen thread also discusses this tension between having a small, curated, thoughtfully distilled artefact, and having a rough, raw, immutable stream of imperfect events, capturing everything about the process.
In my view, deeply understanding how and why a tool evolved a certain way can not be solved with technology alone. Just capturing all the data (git commits? pull request comments?) is technologically possible, but I think the valuable part is reflecting on the process and what forces drove you to make certain decisions. I believe this is not something that can be done up front: Pull request comments of design decisions make sense in the moment, but you are always smarter afterwards. People learn, their opinions evolve, and dumb decisions are only obvious in hindsight.
I resonate most with the idea of building small, cozy artefacts, but explicitly reflecting on the process and documenting important historical decisions. This act of reflection and understanding what drives a project is something active, first-class, and not something that can be captured automatically.