When Jerry and Marge are explaining to Steve that they'd buy 312,000 tickets, Jerry says that it will take "four days of betting, two machines, twelve hours a day". Earlier, it had been established that a machine prints 1,000 tickets per hour. 312,000 tickets on two machines would take 156 hours, which is 13 days when printing for 12 hours per day.
Tyler has his classmates filling in lottery cards each Winfall week, although those cards are reusable and only need to filled in the first time. This is because they are increasing their stake every time - they will always need additional cards for the additional bets.
When they are playing cards, he puts down his hand like he is playing poker. They tell him they are play gin. Gin is not played with 4 people sitting across from each other and the number of cards are not correct for gin.
When the town buys all the tickets for the final drawing, it is to Jerry's surprise. Problem is, where did all the investors get the hundreds of thousands of dollars to buy all those tickets since Jerry didn't give it to them.
Jerry mentions to Steve that the stock market is gambling because there's a risk of loss.
Jerry fails to recognize that investing in many stocks (like buying many Winfall tickets) nearly eliminates the risk.