I know, I know, it sounds very complicated. The actual end goal however is to show quantitatively why estimating too far out is generally unreliable as well as the associated combinatorial explosion of paths. The idea is basically to illustrate the actual reality of planning.
Have you read "Righting Software" by Juval Lowy? You might really enjoy it based on your feedback above and here. There is a project design aspect that goes into this kind of planning (or at least reminds me of what you wrote).
