On "Amateur Night", Patrick bursts into the bathroom totally naked. When he and Clint go back to the room and Patrick falls on the bed however, he can be seen wearing underwear. When they retreat back to the bathroom, Patrick is nude again.
In one of the first dialogues, one of the burglars asks the camera man which tape he is recording on. Around the same time, the irregular cuts to the attempted sex tape start, implying that burglary is being recorded over the sex tape. However, the cuts to the sex tape always pick up very close where they left off, even though the recordings in between usually take up more time than that.
On "10/31/1998", one of the characters, the Soldier, was wearing digital camouflage pants. Digital camouflage did not come out until after 2001/02.
On the "10/31/1998" segment when the guys are heading over to the Halloween party, the cars on the highway are obviously more modern for the late 1990s - early 2000s; a Ford Edge is also visible.