As a Fool, you have to take Fortune's Fool during creation. I think I'm going to try and patch this, since currently it's better for non-Fools than for Fools.
For the Skinflint, Pinch Pennies causes your max Omens to change as your savings change. So if you gain $1,000, +1 Omens. If you then lose that $1,000, -1 Omens.