Earlier quoted context omitted.
I think there are two motivations that get blurred pretty quickly: a) you find a particular context that executes well and want to preserve parts of it or not have to repeat explanations b) you want to continue a session so you don't have to rebuild the context from scratch I think A is something where it's totally reasonable to preserve pieces as part of like a prompt library or equivalent, or directory-specific age…
I think the answer for both cases is supposed to be finishing a "good" session with "based on what you've learned about this project, please update the CLAUDE.md/AGENTS.md/README.md files." Ideally that replaces the back and forth cycle of it's this, no it's that, it's that for reasons XYZ with a single ingestible blob that gets the agent up to speed.
Sometimes it's better to dump context incrementally, reinitialize the agent with a subset of the context, or manually prime it, then ask it to write documentation as a focused task.