ESTP would be my second choice for Chance, however, he seems too damn reactive to be a T. Far from a nice guy, but he seems very emotional nevertheless. I saw a lot of similarities between him and ENFP New York and ESFP Flavor Flav.

One change I would like to make though
Real: ISFJ- he's a lot more levelheaded than most of the other people on "I Love Money" (even though that's not really saying much), even some of the T's, but that doesn't mean he is a T. He has too strong of a romantic streak to be a T (the whole thing with Hoopz).

Mr. Boston, it's tough to say whether he's an SJ with inferior Ne or an NP with inferior Si. In an earlier post I suggested either STJ or NTP. I think an F would have been able to detect what another person is actually feeling at this point of time. T's are exceptionally bad at this. For some reason, I could see ISTJ- even though I don't know of an ISTJ who would act like him- come to think of it- Boston is a man of his own. I'm still going to go with ENTP. I know of definite ENTPs who use their 'chameleon' Ne to try to fit in to society. Many ENTPs see this as the best way to be able to remain with people, an ENTP would come across as more awkward than an SJ for two reasons

a.) SJs are just more common. If an SJ happens to make things awkward, it would be done in a way that other SJs could relate to and not care about much. Boston's awkwardness isn't your typical awkwardness. Everyone gets a little awkward once in a while.
b.) The SJ has that Si (whether its dominant or auxiliary) which helps a person pick up on social cues. The ENTP doesn't have anything to help him out.