... Yeah it's possible. Actually, I borrow from him 1000 caps before to kill him. He says something like "you've got ten days to give me back my money". Then I come back to his place with delay, I talk to him and say I won't give back the money and he tries to kill me. In this case the Police won't do anything.
LightandDark said:
Hell, can I even draw a weapon without them going hostile on me?
Trying to open the door to his back room also gets him mad. As long as he initiates combat, the police don't care. You can piss him off the first time you talk to him, but then you don't get extra cash from the loans.