This is very odd, since I also wrote the meta for Dean in “Bugs”. Of course, you can’t understand one side of the equation without the other, so I’m going to borrow from my meta for Dean and use it for Sam.
There is an element of law vs. lawless for Sam in this episode. He asks Dean if they could get real jobs once in awhile, and Dean replies that they already have day jobs and the pay is crap. Sam notes hustling pool and credit card scams as some of the illegal things they do, but we’ve also seen Sam pick locks, so it’s not just Dean and John who have this illegal aspect to them. Sam, our lawyer-to-be, grew up trying to be normal in “our” world, but was kept in the Winchester version of “normal” until The Fight where John kicked him out. The ‘kicking out” is a little vague; in the pilot Sam references, “Dad said if I was going to leave, to not come back.” As Dean also points out to Sam, there were a few choice phrases from Sam in that fight.
Back to Sam and his morals. When Dean questions the neighbors under the guise of free BBQ, and then squatting in the empty house, Sam raises objections but goes along with him. In the pilot, Sam calls in a fake 911 call to give Dean time to escape the police station. Does Sam have the same moral blinders that Dean does when it comes to family? Hell, they carry a trunk full of guns and other weapons, and who knows if they’re legally obtained? Not that Sam is as morally ambiguous as Dean, but he does have his moments, but they’re justified in saving the family.
Each episode has expanded Sam’s view of what he knows of their dad vs. what Dean saw/experienced. In “Bugs”, Sam comes out and says that dad saw Dean as “perfect”, and was always riding his ass about wanting to play soccer instead of learning bowhunting.
Sam relates to Matt and his strained relationship with his dad. Dean literally gives Sam a blank stare when Sam remarks that the yelling between Matt and his dad looked familiar. Dean states that dad had to raise his voice at Sam when he was out of line, but dad never treated them “like that”, I assume with disregard for how it looked to outsiders to haul your son away from neighbor’s eyes and berate him quietly (though still in plain view). To Dean, dad never disrespected them. “Respect” is noted several times in relation to Sam and John by Dean, and it’s almost a puzzle to Dean how Sam could have thought otherwise.
When Dean tells Sam that dad used to drive by Stanford whenever he could to make sure Sam was all right, it looked like it just shattered Sam. His eyes have a sheen on them during this entire exchange of Sam’s belief that their dad may not want to even speak to him when they find him, and Dean’s rebuttal that Dad was never disappointed in Sam, and respected Sam.
Sam and Dean argue about family when Sam encourages Matt to leave home in two years, when he’ll be able to go to college. Dean thinks that family should stick together. All Sam wanted was normal, and from what we hear from Sam, all he got was flack about it. Listening to an “outsider’s” perspective, in this case Dean, provides a different viewpoint, and enables Sam to distance himself from the skewed by time memories and see another side of John.