Okay, so having too much information about your future was dangerous. The more knowledge you had about it the more you risked changing it. Sam would've liked to think he understood that and was smart enough to be able to handle it, but in reality when it came to his brother he didn't exactly stick to the rules when it came to not changing things that shouldn't be changed.
Sam rolled his eyes. "Sure, Dean, hilarious. Though not exactly helpful if we were relying on him being from a point in time to be able to help us." Help them do what? Both get back to realities that neither of them really wanted to get back to? But without that to focus on what else was there? Besides getting drunk and hustling pool as Dean suggested. It didn't even seem like they could hunt here, from the vibe he was getting about 'everyone having a chance.' Though if Crowley did show up Sam wouldn't so much give him a chance, a head start maybe but not a chance.
Sam returned Dean's smirk in spite of himself, even though he didn't think it was particularly funny, Dean's mood was somewhat infectious and despite the circumstances Sam was actually glad of this downtime with his brother. "It wasn't exactly in the intro but it was sort of implied. I know old habits and all that but it's not like we can get the hell out of dodge when the locals catch on. People don't exactly take kindly to being swindled. Or dwarves don't, I guess." Sam made a quizzical expression, not sure if he was really able to give an opinion on what dwarves didn't take kindly to.
He didn't relish the idea of actually living with Jo, not til he resolved his guilt at least, but he wouldn't have felt right not living with Dean so his hands were pretty much tied. "Yeah, that probably makes sense." He said, which was the truth really, if him and Dean and Jo were all from the same world then it was probably a good idea to stick together. He returned Dean's 'look' with one of his own, finding gainful employment wasn't anything either if them was used to, though they'd both done it from time to time. "Looks like, I mean there doesn't seem like there's much call for our particular area of expertise."