Alex's teacher claims to have voted for FDR 4 times, which would have been every time he ran for president with the first time being in 1932. This episode is set in present day (1983). That is a 51 year difference. The minimum voting age in 1932 was 21 years of age. Therefore, Mr. Wilkerson would be at minimum 72 years old in 1983: a bit old to be teaching high school.
While the family is playing Monopoly, Alex says he got double 3's, and then Jennifer says it's her turn. Alex should have had another turn since he rolled doubles.