He sounds like an enneatype 5.I asked my ISTP about this last night. He told me that he doesn't see himself as rebelling or doing anything just for the sake of being deemed rebellious.
He simply acts on his own whim regardless of how it is perceived by others, society, or the law. He has no problem following the status quo as long as it appeals to him, ie makes sense. But this is rarely the case as he sees large numbers of people as insane, tribal-collective mentality as dangerous, and many rules in place not because they make sense but because they result in revenue collecting and control. He abhors social expecations and norms for the most part.
He sees no reason to take strong stands against society as it usually entails more bullshit and aflliliations with yet another mob mentality. He finds the most productive and unproblematic way to retain freedom is to keep a distance from most people unelss they follow the same line of thought. His best friends are other ISTP's and ESTP's.
He also has a morbid sense of humor and I have to chastise him freqently for laughing when a parapalegic falls off their hover-round, a 7 year old biffs it on their bike, or when some idiot playing with guns shoots their foot off. At the same time I have caught him doing extremely kind, humanitarian actions.
In a way I kinda admire the sense of equality he holds. He doesn't look down or up to anyone. He is extremely non-judgemental.. It doesn't even occur to him to judge people based on apparance, status, money, intelligence, or social skills. He's definately one of the most authentic people I've come across, and I think this links back to him giving a rats ass about how he is perceived.
ISTP's are cool cats, to be sure.