How many times have the Simpsons blown their chance at riches? I can think of:
1. Half Decent Proposal 2. Tomacco 3. Bobo 4. The greyhounds 5. Burns hits Bart with the car 6. The electric hammer 7. Designing the car (not rich per say, but $80,000/year + rich brother) 8. Going to work at the other plant (forget the name) but better pay, nicer city, self-cleaning house, etc. 9. Was there a reward for the babysitter bandit or just the t-shirt?
Anything else you can think of?