Stupidity: You'd think that Jezzie would have been a little smarter as a secret service agent. You know, like once they acquire Megan, to delete all the incriminating evidence sitting back on an unattended computer. Aside from the fact she also used quite a stupid password, a single password isn't very secure at all. And then the content, displayed instantly when you get in, might as well say things like "hey look, we know what the kidnapper looks like" and "wow, here's the boat he's in too" and "wow, a cabin for sale. Why don't we go hang out there with all the evidence." Come on....they might as well have left a trail of breadcrumbs, because they sure were asking to get caught.
Stupidity: Mercusio is looking through FBI files on his computer. The FBI has a horrible database then, since the agents' postings are listed all in random order (otherwise Ben would be working at the White House and not at the school - which is also suspiciously listed without any hint about its location). (01:11:30)
Stupidity: Mr. Soneji's class is so advanced that they use encrypted files to pass each other notes and whatnot, but their assignment, which takes them a long time to complete, is to "find the official website of Charles Lindbergh." Even in 2001 with search engines not quite well developed as they are now, it wouldn't take them the minutes it is taking here, especially with the whole request being designed as a contest.
Stupidity: The sequence when Tracie is found out does not make sense in the way it happens; how does grabbing someone to solicit a blowjob involve sticking a finger in the ear of the opposite side? Also, the earplug is shaped and made to look like a hearing aid, so the trained agent that she is should really have that as an easy answer when she is found out, especially considering that her hair is short and styled in a way that makes it entirely possible he could have noticed it when he picked her up in a better lit place than the car (in fact she should have brought it up first to avoid suspicion). In fact, the 'sticking finger in ear' gesture makes sense only assuming he did not just find out but had spotted the earplug before. In that case, he could only have noticed before having her in the car, so he would have not picked her up to begin with. (00:04:00)