This vaguely seems cool in that I've always wondered, when making day-to-day predictions, whether the amount of money matters. That is, sure, I'll mentally predict a 70% chance that the cafeteria has chicken today, but how much would I bet at 70:30 odds? I get the sense that your proposal here would help me tease that out.
However, in practice, my eyes glaze over when reading the described scenarios. (Sorry! I know you tried really hard.) Putting a single probability number on things is already a hard enough skill to develop. Figuring out a potentially-escalating series of bets, based on wild-ass-guessed utility dollar values? Or, apparently as an alternative formulation, saying I'd "35% do something"? I haven't internalized this concept, and I doubt many other people in the community have either. I think it'd be difficult to get adoption for anything built here, without first percolating the idea through the blogosphere for a few years.