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Mr. Monk and the Astronaut - S4-E14
Stupidity: Steve Wagner is shown expertly constructing an elaborate hanging machine, but he adds a superfluous complication by having it triggered by a garage door remote control that he posts to the address in question. Anything could (and does) go wrong! Why doesn't he simply have it triggered by a bog standard timing device that you can buy in a hardware store for a tenner? I am not sure I'd trust him with my space shuttle.
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Stupidity: After talking to the bartender, Calleigh goes back the lab and talks to Caine, and he wonders if they got a false positive from the vic's blood alcohol. Calleigh then gives a detailed description of how that could happen; Caine already knows how (obviously this was done for the audience, to explain it, but in the context of the show, it makes no sense).