Mr. Monk Meets His Dad - S5-E9
Plot hole: Monk's dad, Jack, drives an 18 wheeler. In the scene where Jack pulls over to the side of the mountain road so they can discuss specifics about the GPS, a brake line is shown breaking and spurting what I assume is meant to be brake fluid. The rig then rolls down the mountain. However, 18 wheelers don't have brake fluid since they don't have hydraulic brakes, they have air brakes. Even if the rig lost its brakes due to loss of air pressure, the brakes are spring loaded to lock up all the wheels in this case and prevent movement. That's how you set the parking brakes, by releasing the air pressure. In other words, if he has air, he can use his application brakes; if he's lost air, he has his parking brakes set. Rigs that lose their brakes going down steep grades do so due to extreme overheating, causing brake fade, an inability of the brake shoes to grab the brake drums. This wouldn't have happened while they were parked.
Mr. Monk and the Really, Really Dead Guy - S5-E15
Plot hole: In this episode, Monk doesn't know to open a cell phone to answer it, but in "Mr. Monk and the Kid", he used a cell phone with the ransom drop with no problems. (00:04:25 - 00:05:05)
Answer: Stottlemeyer was already upset after the phone call. He was trying to get "Kevin" (who would have to be a judge, but no further character information is given) to issue a restraining order with no evidence of needing one, except that Adrian Monk said she needs one. Kevin said he would need to "sleep on it." So it's clear they've been trying to provide protection and unable to get the results they need, which seems to be based on no one trusting Monk the way Stottlemeyer does. He's just angry that they failed to protect Linda despite all their work. Although it does feel like a scene was cut, or altered, from the show that shows the futile attempts to protect Linda which built up to his outrage.
Bishop73