Factual error: In the flashback where Monk is explaining how the money was stolen, the principal finds the 5 dollar bill he wrote "good luck" on and holds it up for everyone to see. The bill he holds is a 5 dollar bill which was released in 2000, with the enlarged Lincoln. The flashback takes place in 1972.
Factual error: When Monk is talking to Sherry about the painting in the art gallery where the painted woman was going to kill her husband, he says that she has a bruise on her left eye. But the bruise is actually on her right eye. While it is viewable that it is on Monk's left, he would not make that mistake.
Continuity mistake: When Monk is doing the summation for the present-day case with Sherry's ex-husband sitting in the chair, at first you can see that the painting is directly behind him. However, shortly thereafter during the summation, the painting has somehow shifted to the viewer's left and is no longer directly behind him. While it's plausible that someone could have moved the painting, it's just not believable since less than a minute has passed. Besides, would Lt. Disher (he was closest) really take it upon himself to move evidence?