Per dad's interview, he assumed that Dylan was visiting a friend nearby. When he woke up at 2:30 and Dylan still wasn't home, he became concerned. I'm not claiming that Dylan's parents let him run wild, I'm looking at what we know.
His mother said that he visited friends and sometimes didn't touch base until the next morning. His father said that he had a history of hitch hiking (that he was unaware of until the disappearance). That sounds like an independent child whose parents trusted him to make good decisions.
It's not uncommon for a couple of hours to pass between the last time a teenage child was seen and a missing person's report. In this case, dad assumed that Dylan was nearby and it wouldn't have crossed his mind that Dylan had hitch hiked. 2-3 hours passed and then the alarms went off in his head.
Interesting that you and I have such a different take on this.
From the quote from ER of "he would let me know where he landed for the night. So like, if he was hanging around with his friends in Bayfield, you know, he would let me know what friend he was sleeping with that night", you get that he would not touch base, and I see exactly the opposite, that he WOULD touch base and say which house he was at that night, not the next morning.
From the statement of a friend that he got a ride home home for the entire group by sticking his thumb out one time (not multiple times, just one), but his father SAYING he had a history (which has not been substantiated) to you makes him a habitual hitchhiker. History to me is "An established record or pattern of behavior", not a one time event. And grabbing a ride in the snow with your buddies is considerably different than picking up a ride by yourself when you know your ride is coming. (not to say that it couldn't happen, just that there was no history of that)
And while I do agree that it's not uncommon for a couple of hours to pass between the last time a teenage child was seen and a missing person's report, I find it a little uncommon that a father knows his son wants to visit friends in another area, that he is supposed to be the ride, and thinks nothing that his son is not sitting there waiting, chomping at the bit to get his ride. I trust my son to make good choices, but I'd still check to see where he went if I knew I was supposed to drive him somewhere. Otherwise, I would be shirking my responsibility. To just go, "Oh, well he's not here, now I don't have to drive him so I'll take a nap." would not be on my particular radarscope. But that may be because I have a 13 year old who behaves a certain way and I would know what would be odd for him.
It's so weird that two people can read the same thing and get two different impressions out of it, but there you go.