Assuming that his Silk Road days were behind him: Would you share a flat with Ross Ulbricht? Would you trust him not to put a hit on you for drinking the last of the milk or spending too long in the shower? Could you be his friend?
Assuming he'd left office: Would you share a flat with Barack Obama? Could you be his friend?
Question number one answer yes I would share a flat with him and not worry about drinking the last of the milk or having really long showers, he more than likely is not the type of person made out to be and if he is that also does not matter I'm not afraid of a quick death like a hit would be.
Saying that I don't want to die for drinking milk lol but that would not stop a friendship being built and not based on fear yes indeed could be his friend. Obama if he wasn't a puppet for the money then yes would also be his friend/flatmate.