Plot hole: Just how can you get a famous author, a judge, and a flight attendant set-up Adam Sandler in such a scheme? A judge cannot use a courtroom (along with bailiffs during regular business hours) to pull off such a scam. Moreover, when he was arrested for the fight in the bar, there is no guarantee he would have been brought up before the same judge. Also when explaining to his boss about not getting a second flight in the beginning, Adam Sandler says that the plane had been turned around because of his behaviour. Show me an airline that's willing to do that for a scam.
Plot hole: Near the end where Adam Sandler's girlfriend tells him that the anger management was a set up, Sandler asks about the air stewardess incident and she says that it was all a set up, however, the cocktail waitress incident isn't mentioned and surely his girlfriend couldn't have arranged that, therefore it was in fact a coincidence that everything worked out in the end.