Probably most people wouldn't -- I think that was kind of the point. The whole place was built on oppression (psychic/psycho Mayor) and repression (Sam and the townspeople).
I liked the idea of a town living in a delusion, and that the psychic was just some random mostly-human monster. That felt like a throwback kind of MoTW idea, especially how it was meant to tie in with Sam's state of mind, and I wish the show would go back to doing more of that. It was also fun how the town had such a sense of place. That also felt like a bit of a throwback to earlier days of the show, in a good way. And usually Cas is boring to me, but I liked him in this episode. Like when he matter-of-factly asked the clerk, "Scanners I, II, or III?" LOL who the hell has even seen Scanners? I've seen a lot of movies in my time and I didn't know about that series at all.
What didn't work for me was that climax when Cas and Sam fought and Cas made Sam come to his senses. Cas's arguments just didn't seem that moving, and I was kind of surprised that Dreamworld!Sam would even be up for randomly stabbing people to death in the diner anyway. Like really, I would have been like, "You're not a murderer! You're not a puppet!" Not "Sure you were a failure as a leader, blah blah blah." Seemed like a weird (and unpersuasive) tact for Cas to take. I also wasn't feeling Cas and Sam's chemistry this episode. I actually usually like them together, but for whatever reason it wasn't quite gelling.
Dean and Jack's scenes were incredibly awkward, and sometimes that was actually pretty funny but sometimes, eh. They did seem to drag. The scene when Donatello tries and fails to impart some soulless wisdom onto Jack especially should have been more interesting than it was -- nothing was *wrong* per se, but it just seemed so drab. Also, Donatello is just such a tragic figure to me, and he's an interesting character in general, so I feel like he was kind of weirdly wasted in this episode. I agree that he's more interesting than Jack, so I would have been more interested in a story about Donatello that maybe also led to Jack learning something or led to everybody else also getting insight into Jack or something like that. But really, the one of the few spinoffs of SPN that I would legitimately be interested in would be the adventures of the prophets, especially Kevin (and/or AU!Kevin) and Donatello, because I do find being a prophet really tragic and difficult and interesting in the show's universe. So maybe that's just me.
Otherwise, some of Dean's "comedy bits" were pretty funny. I laughed when he opened the carton of leftover Chinese food and found mice inside, but tried to play it cool. And when he made some weird face to himself in the car after yet another incredibly awkward conversation with Jack. It was kind of funny to me that Dean was finding his interactions with Jack as awkward as everyone in the audience must have. I did find that Dean was written really oddly in this episode, though. So upbeat and childlike? I mean, not that he did anything that out of character, it just all had an odd tone.
And I thought that it was genuinely disturbing when Jack put the snake "out of its misery" by turning it to dust in his hands. What was creepy is that he wasn't being malicious at all, but it was still just such an inhuman thing to do. I think part of the point of Dean being grossed out and creeped out by everything was to show how cold and "alien" Jack was acting in comparison, but it was too ham-handed and over the top to really work. Same thing with Dean constantly wanting to eat and Jack never wanting to eat.
That said, the only joke that I actually disliked was Jack choosing the angel v. devil cake. The show played it up way too much and the joke wasn't clever enough to handle that kind of attention. Also, I wish that instead of devil's food cake, they had used Flaming Hot Cheetos or something. And maybe the "angel's food" could have been some sort of ambrosia pudding. To be fair, though, maybe my distaste is because I find those kind of packaged cakes gross. Like if I had been Jack, I would have been like, "PASS" on those choices, soul or no soul.
Oh, and I was really excited for a minute near the end when it sounded like they were going to leave the bunker and go back on the road. But then, nope. Really too bad. I mean, honestly, Sam did have a point that the bunker has lots of terrible memories in it. This wasn't even the first massacre they've had there. Plus, I like the road trips and the motels and stuff, and I miss them.