Plot hole: After the car burns, and they arrive at the motel, Neal only has $17.00 on him and nothing but melted credit cards, forcing him to give up his watch to help pay for the room. Del only has $2.00 but his watch doesn't quite flip the bill. At this point, between Neal and Del, they only have $2.00. However, when Neal invites Del into the room, so he doesn't freeze to death, they are eating Doritos and drinking shooters. Even in 1987 Doritos and a bunch of shooters must have cost more than $2.00. This is assuming Del didn't already have them in his trunk. But even if he did, at the end, Neal gets on his train, makes a return trip to find Del just where he thought he'd be, and then they'd both have to get back onto that train. After all, they both showed up at Neal's home. Once again, It would take money to get on that train. Four train fares with only $2.00. Neal's first trip, return trip, and Neal with Del for the last trip = four fares.
Planes, Trains & Automobiles (1987)
1 plot hole
Directed by: John Hughes
Starring: Kevin Bacon, Steve Martin, John Candy, Michael McKean, Laila Robins
Continuity mistake: When Del comes out of the passenger side of the dairy truck, he is with a black eye, for no reason. The next scene, it is not there. It is there again when he admits to being homeless. (Steve Martin punched Del in a deleted scene.)
Bus Lover: Why don't you take a picture? It'll last longer.
Trivia: When Neal's wife is watching TV in bed, she is impossibly viewing the John Hughes film "She's Having a Baby," which didn't even premier in theaters until February of 1988, three months after "Planes, Trains and Automobiles" premiered in November 1987. John Hughes (who directed both films) used his own unreleased "She's Having A Baby" footage/soundtrack and a cameo by Kevin Bacon as teasers for the upcoming 1988 film. There's still some speculation that the plots of the two films actually intersect, and that Kevin Bacon (who is credited as the Taxi-Racer in "Planes, Trains and Automobiles") was playing his character, Jake, from "She's Having a Baby."
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Answer: He's not homeless, he has a house or an apartment somewhere, or lives out of hotels. He just no longer has a 'home', ie, a place where he's happy and someone loves him.
Brian Katcher