Stupidity: There were three vehicles parked in front of Rosie's Cafe when the Virtuoso arrived before 5:00 PM. As he walked past the vehicles, he surreptitiously took photos of the license plates to help him identify the likely target. The Waitress' Jeep was parked apart from these vehicles, on the side of the restaurant. The Virtuoso went by the restaurant's front windows where the target possibly could see him and took a photo of the Jeep's plate. (The fact that no-one noticed is irrelevant).
Stupidity: A majority of what the Waitress did was highly questionable, but her manipulation of and reliance on the Virtuoso to kill the (impostor) Sheriff (in particular) was foolish and could have very well led to her not being able to complete her mission. The Waitress made the Virtuoso become suspicious of the Sheriff by saying there was something "off" about him and his badge didn't look real. Believing he positively identified and killed "White Rivers", the Virtuoso could have easily left the area.
Stupidity: Throughout the movie, the Virtuoso did many things that were contrary to being a shadow and not leaving any evidence of his presence. For example, he often wore gloves, but not when picking up a knife in Rosie's kitchen. Each time he went into the motel office, he interacted with the clerk and called attention to himself by asking for coffee but leaving before the clerk returned. He fell for the Waitress' advances, met her after the restaurant closed, and let her come into his motel room.
Stupidity: When formulating his plan to kill the CEO, the Virtuoso posted "lost dog" signs on poles within the area he was going to shoot. When finished, he looked up and across the street to the window from which he was going to shoot. Instead of being "a shadow", the Virtuoso put himself at the crime scene the day before, looking quite suspicious. If/when police looked for surveillance camera footage, the Virtuoso's behavior would be quite obvious. (00:10:23)
Stupidity: After the Sheriff was shot in the neck but was able to run into the woods, he hid behind a wide tree trunk. He shot at the Virtuoso but missed. Instead of staying behind the wide tree trunk and shooting again as the Virtuoso advanced toward him, he flees from tree to tree where the trunks are not as wide, giving him less protection and more of a disadvantage. Eventually, he is killed by the Virtuoso. (01:21:48 - 01:22:26)
Stupidity: The Virtuoso was given very limited information - that he should go to Rosie's at 5:00 PM. While there, he thought "Something's not right" and "Without the Deputy, you [the Virtuoso] could complete the assignment. The outcome would look like a robbery gone wrong." Still unsure, he decides to "give it more time", watches the vehicles leaving Rosie's, rightfully assumes the Loner will go to the motel and follows him. BUT the Sheriff left first, meaning he could have gone back to finish the hit. (00:35:25)
Stupidity: After suturing the woman's gunshot wound in the barn, the Virtuoso finds a space heater. He sets the space heater on top of a low stand of some kind and then uses an extension cord to plug it in - two things that should NOT be done when using a space heater. Also, there is sound as though the space heater is running, but there is no change in color (coils turning red) that would indicate it is on and heating. (01:12:44 - 01:13:06)
Stupidity: The Virtuoso drove to the farmhouse and parked behind the stable, but did not entirely conceal his car from the house. After he got there, he selected weapons/guns from the trunk - something he (a "professional") should have already decided and prepared before arriving. (01:05:07)
Stupidity: The Mother who got engulfed in flames from the car crashing and exploding on impact with the van stood around flailing her arms and swinging her purse (also on fire) instead of doing what "everyone knows" to do: drop and roll. (00:12:19)
Stupidity: The Mentor told the Virtuoso that the murder of the CEO needed to look like an accident. It was acknowledged that 48 hours to plan the hit wasn't enough time, but it had to be done. The Virtuoso - supposedly an "expert" - decided to shoot the front tire while the CEO was driving past the building, making him "overcorrect" and thereby slam into the building. Even IF this would have killed the CEO, a BULLET HOLE to a front tire would not look like an accident. (00:09:22)
