Okay, I'm going to try again to put all of my thoughts, theories, explanations and whatever into one post, and see if I can come up with a feasible scenario.
Dylan was texting with R from home and the airport before his flight. Mark picked Dylan up at the airport shortly before 6 pm. Dylan sent a text to Ryan saying his plane had landed, and they talked about their plans (from the article that included copies of their texts). They went to McDonald's to get something to eat and then to Walmart to get food for the visit. While they're there, Dylan asks about going to Bayfield that night, and Mark says it's too late for visiting that night. At about 6:45, R asks if he's coming. Sometime around 7:00 Elaine texts to see if he was picked up. At 7:06, he responds to Elaine saying yes with a "scowling" face. At 7:09, he tells R that he can't go that night. Mark and Dylan head for home, and discuss the possibility of Mark dropping him off in the morning before his appointments.
More texts are sent between the boys, and shortly after 8 pm, Dylan stops responding because he's still trying to work things out with Mark, possibly whether he'll be spending the night with R or going back home at night, what time he'll be picked up (if he has to return), when he'll have to be up if he wants to go in the morning, etc. They get home, and go inside. Mark throws the football to Dylan, trying to cheer him up, but Dylan just throws it back at him and plops down on the couch . He turns on the tv and falls asleep.
The next morning, Mark tries to wake him up, but he's still tired and cranky. Eventually he tells him he'll have to go now or wait until he gets back. Dylan tells him he'll wait (in whatever words they used), and Mark leaves at 7:30. Dylan wakes up at about 9:00, turns on the tv and gets a bowl of cereal. He decides he doesn't want to wait for his dad to get home, so he goes outside to see if he can see anyone around who could give him a ride. He tries to call R to let him know, but realizes that he fell asleep without putting his phone on the charger and it's dead. About that time, someone comes by and sees him out there. Since he knows that one of Mark's vehicles is gone, he assumes that Dylan is alone. He stops and asks if Mark is there, and Dylan says no, and then complains about having to wait until at least 11 for a ride and that his phone is dead.
The guy offers to take him to R's house, and Dylan accepts the ride because he knows the guy lives around there and knows his father (since he stopped supposedly looking for him.) I think the fishing pole is just a fluke - Mark is out of town a lot, and some kid could have taken it without him noticing it was gone until he was looking for Dylan.
All just my conjecture, but I'm trying not to make too many assumptions.
