Plot hole: Jim leaves to attend his family Christmas as evident by his dialogue in the opening scene, and evidently Carl is supposed to be at home to his family in the morning as well, but both are killed by Thomas. When the movie ends with Angela entering the city, it is early morning just before sunrise. Jim and Carl's families would have noted that they were not home on time, and therefore would have had someone searching for them. This makes it implausible that Angela's situation would not have been discovered.
Plot hole: In the yearbook scene Tim barges into Jamie's room and asks her to sign his yearbook, pushes Chris off the bed, and they somehow get their yearbooks mixed up. Tim's yearbook is left in the room with Jamie and Chris, while Tim takes Jamie's yearbook that Chris wrote in with him. When Chris asks Jamie to read the message he wrote in her yearbook, she instead reads the message that Tim wrote to her in his own yearbook. If Tim was asking Jamie to sign his yearbook, why would sign the yearbook with as if he was signing Jamie's. If he was intending to sign Jamie's yearbook, he would have written in the same yearbook that Chris wrote in and not his own.
Plot hole: Near the end of the film it's revealed that Drew grew up poor with only his mother, who had to work double shifts to survive. So how did they afford that huge house? Even the Valcos are supposed to be struggling financially yet they now live in this massive house too.
Plot hole: It's never explained how Ms. Pearly the landlord knew Craig and Day Day since they were kids, and it also doesn't make much sense how Craig and Day Day are so scared of Damon and can correctly recall him being this super buff grown adult, when he was locked up for 12 years and their characters are all in their early 20s.
Plot hole: When Bill and Clark are discussing the bonus delivery situation, it is December 21st, and Bill says his son received a delivery at his home via company courier. The bonus checks were to arrive to the employees before Christmas Eve, which would have given them plenty of time to contact each other that none of them got the bonus checks but did get enrollment in the Jelly of the Month Club.