Pretty interesting idea, Castle.
There are some devils in the detail I think. There is bound to be a perfect level, where you win the most by paying the least and the perfect level of progressing the fastest (what do I have to pay to win most - level)
As a dev you would either have to very consciously set those levels or have them occur randomly. The latter is quite dangerous I think.
All in all this still sounds like a very fresh approach with a lot of potential. I would help you crunch some numbers if you wanna develop the idea further.
Yeah it will require a lot of planning and thinking to get all of the details in place. I may consider making a prototype once I complete Revulsion Episode 2 content.