I wonder if documentation would help to create an carefully and intentionally tokenized overview of the system. Maximize the amount of routine larger scope information provided in minimal tokens in order to leave room for more immediate context.

Similar to the function documentation provides to developers today, I suppose.

It does, shockingly well in my experience. Check out this blog post outlining such an approach, called Literate Development by the author: https://news.ycombinator.com/item?id=43524673