When Frank is being questioned by the school's auditor about his flights to London, the auditor mentions Frank had booked first class on Concorde. In reality all Concorde seats were the same class, so there were no first class.
When Frank is on the operating table the surgeon cuts directly into his hairline. This is unheard of. No surgeon would ever cut into skin with hair growing out of it.
At the craps table, they guy says he needs a "hard eight" but then calls for "box cars", which is completely different. "Box cars" is a 12, and "hard eight" is a 4 and a 4.
In Las Vegas at the craps table, the player shakes both dice together cupped in both hands. No craps table dealers would allow that...they ALWAYS insist players hold the dice with ONE hand.
The movie is set in 2002 - 2008. Several more modern cars can be seen driving and parked in street scenes.
There is a scene where Frank is driving though Greenpoint, Brooklyn. In the background, you can see the new Kosciusko Bridge, with multi-colored lights, which wasn't rebuilt until over a decade in the future.
In a scene where Frank addresses the school board in a conference room, in the background there is writing on a dry-erase board referring to a "DASA complaint." The scene takes place in 2002; DASA refers to New York's Dignity for All Students Act which was not signed into law until 2010.
Various characters are shown using Motorola Razr cell phones in scenes that take place in 2002. The Razr was not introduced until 2004.
Pam's New York accent comes and goes.