Mr. Monk and the Other Woman - S1-E8
Plot hole: Monk's led to the killer because he figures out that he "added a file" to the lawyer's filing cabinet, judging by the left/middle/right tabs being off. But this makes no sense on two levels - firstly why would he need to add a file? He was just replacing the real will with a forgery. He just took the old one out and added the new one, he didn't need to mess with the filing system at all. Secondly, he picks that one out because the tabs are offset, but what if the lawyer had just taken on a new client or added other paperwork? Then the tabs would be off too, but that never seems to be considered.
Mr. Monk and the Other Woman - S1-E8
Plot hole: Monk says that the two files, both with tab at the middle, were kept together, which led him to discover that the person related to this file is 'the guy'. In an earlier scene, when Monk is searching the file cabinets, he picks up one of these two files and tells Sharona that this file is of 'the guy'. How can he say which one of the two files with middle tabs, which are put together, is related to 'the guy'? Impossible. (00:39:00 - 00:40:00)
Mr. Monk and the Other Woman - S1-E8
Audio problem: When Monk finally turns around at the funeral to tell the old man behind him to be quiet, you can still hear the man coughing. But the man's face is still, and his mouth is not open, and he isn't making the sound.
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