Chuck tries the road trip thing, right when he's starting out with the books. It's basically one long, depressing family road trip, right? He figures he needs to get into Sam and Dean's mindset, to feel how they do every day, driving from place to place with only a cheap bed to rest their heads at night.
Sera calls it an adventure, and encourages it. She says she doesn't need a another book for another two months, and if it comes to him as quickly as the first few did he can take three or four weeks to live their life, minus the hunting.
As it turns out, their life is tiring. Chuck drives aimlessly, through dull farm country, monotonous field of wheat after monotonous field of corn after monotonous field of wheat again. The bland visuals and the empty roads make him sleepy, darkness creeping in at the corners of his eyes. It terrifies him, the thought of falling asleep at the wheel and never waking up.
So he takes a lot of breaks on his trip, sitting in the turnpike coffee shops when he can, and just resting his eyes on the side of the road when he can't. He's not good enough at long-distance driving to trust himself on the roads for hours on end, like Dean and Sam are. Still, he figures even they can't go that long. They probably switch drivers, and drink a lot of coffee.
So yeah, the road trip part of it isn't so great.
The motels are worse.
Chuck doesn't know how they do it - Dean must have some kind of spidey-sense about clean, cheap motels or something, because every one Chuck goes to either costs twice what they pay or has mysterious stains around the room. He can't get any sleep, just thinking about who's been doing what where he's lying. His imagination isn't that good, these books aside, but he doesn't have to work at it to guess what caused those stains.
After almost driving off the road from all the sleep he's not getting in those motel rooms, he buys a blanket and wraps himself in it, lying on top of the covers. He still can't stop thinking about the mystery stains, but at least he knows he isn't lying on them. It's good enough to let him get to sleep, anyway.
Chuck spends two weeks driving in a vaguely westward direction, the idea of going to Lawrence for research at the back of his mind, but by day fourteen is so sick of driving that he pulls a U-turn on the empty back road he's been driving for the last hour, heading for home.
This may be the life for Dean and Sam, but Chuck's pretty sure that the end of their road trip is Crazytown, USA. He'd rather have the comforts of home and a good night's sleep, thanks. As for the books?
Eh, he can improvise. Who's going to notice?
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tm)