So I completely rewrote the system from scratch, changed the dice mechanics, turned it into functionally a new system, and have started prototyping a much larger game with the system that Iterate! will be part of.
Which is excessive, yes, but it did technically fix the first problem.
(Technically)
On the plus side I should be able to continue the quest soon, on the down side it basically snapped the mechanics from the last vote in half and on the plus side again, once I put everything together you will get to reroll!