Mr. Monk Goes to the Asylum - S1-E6
Continuity mistake: The doctor says that Mr. Monk is allergic to tomatoes. In another episode Mr. Monk makes a sandwich with tomato. There is another episode in which Mr Monk is excited about square tomatoes.
Mr. Monk Goes to the Asylum - S1-E6
Plot hole: Monk and Manny go on the roof through Manny's window to grab a piece of cloth. Due to the possibility of suicide, it is highly unlikely that an asylum would have a window that goes directly to the roof, unlocked.
Mr. Monk Goes to the Asylum - S1-E6
Factual error: The woman who accuses Monk of stealing her necklace shouldn't have the necklace inside the asylum in the first place. For both safety and insurance reasons, patients in mental facilities aren't permitted to keep any potentially harmful jewelry, including pins, broaches, earrings, belts, beads and necklaces.
Mr. Monk Goes to the Asylum - S1-E6
Visible crew/equipment: When Monk is on the roof and helping the guy not to fall, you can see that he is tied off with a rope.
Answer: The two men are trying to work out a secret deal between them without involving the union, which means the workers' interests aren't being represented and defeats the whole purpose of a union. The mayor would lose labor's support and Cusack's union troubles would just be starting.
Captain Defenestrator