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I think that Benson thinks his obsession with escaping Maxfield is a reaction to the conditions of the school. However, I see Benson's initial (read -- INITIAL) reaction to the school as a conditioned response. Benson's life has been filled with residences that have always been temporary. As such, Benson's reaction may be to fixate on the negative aspects of a locale upon arrival, with the knowledge that the location is just another temporary setting in his story. Is it possible that his reaction to Maxfield is no different than how he'd react to being in any other new place? That is, that he'd find a reason to not get attached, knowing full well that his stay would not be permanent? Is part of his trepidation with Maxfield the fact that he's never known a permanent residence before, and he does not know how to react to that type of "stability?"

Upon his arrival, he talks about how he's made up a story so he'd fit in there and not be the poor kid everybody picked on. He also talks about wanting to be somewhere long enough to be on the football team, run for office, and get a girlfriend. It's interesting to see him having fun w/ paintball and interacting with Jane, because it mirrors that which he wanted from his other school experiences. He wanted to get attached until Becky wouldn't answer why Curtis and Carrie ran for it.

I think that his reaction reflects his ability to cut through what he perceives as fake and contrived. He initially is optimistic about his arrival to the school. Because his life may not have been filled with rainbows and skittles, it would make sense, that he is grounded in a sense of realism, and, as you mentioned, cynicism. So, when things seemed suspicious, he was quick to point it out. What stood out to me, though, is that he was going into it with a positive mind-set.