Times the Simpsons coulda became rich?
 

There so many, i cant name them all. Lately i only remember when Moe stole the Flaming Homer, and Maggie keeps Mr Burns bear BoBo

Tomacco! And way back in the first season, when Mr. Burns ran over Bart. Got a few more in mind, but I'll leave some for others.

How about Lil' Lisa Slurry?

homer:"i'll take this candy bar and this winning ticket!"
apu: you only have enough money for one.
homer:"fine... the candy bar."

and when bart was heir to the burns fortune

In the 'Behind the Laughter" episode, the Simpsons were so rich that they bought MC Hammer's old mansion.

Homer sells his PowerPlant stock for an imported beer and a hammer...i think

Didn't Bart and Homer make a few bucks in the episode they became con artists?

Beer Baron?

Or when Homer disowned Santa's Little Helper, and he went on to become the Duff mascot.

What were they going to win on the Japanese game show?

Just tickets home.

Maybe the episode where Homer found his long lost brother Herb, who had the car company, until Homer bankrupted the company with his new car.

Or Homer wanted dinner at America Town.

Bart burns Christmas, and people give them charity money.....

Mr. Burns car hits Bart on his skateboard, it goes to court and Mr. Burns wants to settle with Homer and Marge for $500,000, but Homer gets greedy and tries to settle for a million, and then Mr. Burns sees what's happening and rescinds the offer.

When Homer invents the automatic hammer, which is then attributed to Edison.

Wasn't there an episode where Willy wins the lottery and then Alf gets hungry and eatst the ticket? -whoops wrong show.

Didn't they sell their house at some point too?

When santa's little helper has puppies, and in the end mr. burns gets them, and they go on to be million dollar race dogs.