The first time Bob is talking about Monopoly with Mr. Carlin, he talks about having four hotels on Boardwalk. In Monopoly you never have more than one hotel on Boardwalk, but you do have to get four houses on a property before you can put a hotel on that property.
When Bob is describing his Monopoly game, he says his first roll gets him to Chance and he advances to Illinois Avenue. He then says on his second roll, he gets doubles and passes Go. Since Illinois Avenue is 16 spaces away from Go, the only way he could "pass" Go would be to roll double nines, and Monopoly dice only go up to 6.
Howard asks if anyone wants to "take a drive down to the lake and park." Howard and the Hartleys LIVE on Lake Michigan, at 5901 N. Sheridan.