Plot hole: When Jen and Grams are talking on the porch, Dawson walks up to talk to them. They ask him if their cab has arrived, and he says no, but they are in his shot. They then choose that time to say goodbye to Dawson, which turns into a group 'goodbye' with everyone that lasts several minutes. Meanwhile, the cab has arrived, and when they are finished saying goodbye, Grams, Jack and Jen walk to the cab and get in to leave for NYC. But what happened to all their luggage for the trip? How did it get in the cab? They went straight from saying goodbye, into the cab without stopping to carry their luggage to the car.
Plot hole: During this entire episode, Audrey is helping to film Dawson's movie by playing the role of Ms. Jacobs. We already know that Audrey is in the midst of Summer School at Worthington, but she is apparently staying down in Capeside during the entire time of filming. Audrey doesn't own a car in Boston, and it would be very difficult for her to commute every day to school and back. So why would she suddenly take off several days to do Dawson's movie when she is in the middle of Summer School classes? She mentions how boring the classes are, implying they are still going when she decides to do the film. Given that her academic standing is in jeapordy from missing almost an entire semester previously, it doesn't seem likely she would ditch her classes during the Summer to take off and film a movie.
Continuity mistake: At the end of the day, Joey and Dawson are laying on his bed talking. When Joey asks Dawson how he would describe his film, there is a close-up of Joey looking directly at Dawson, who is to her left. The next shot, as Dawson answers, Joey is suddenly staring straight up and not looking at Dawson. Then in the next shot, Joey is again looking back at Dawson to her left. The transitions are too fast for her to have actually moved her head.