Have you seen @sheik’s ideas for creating scores from your boulder positions on the chart? It’s towards the end of the thread here: Basecamp's Shape Up book - #21 by clouedoc
(I tried applying that kind of scoring to my projects but mostly ran into problems of things being badly scoped to start with and projects full of immovable boulders so I haven’t really got anywhere with refining the scoring, or have anything else useful to add but I’m interested to see if anyone else has.)