Ok I've just met Caesar in his camp. Had to send Boone back to the 38 so I could actually go in there.

I want to free Benny by giving him the Stealthboy + Bobby pin he asks for. However, THIS IS TOTALLY BUGGED. Trying to free Benny using using either options he gives you will always lead to the Legion NPCs in the tent going immediately hostile and murdering both you and Benny.

This is game breaking. I cannot keep my character consistent if I either abandon or murder Benny. I would love some sort of solution to this so I can continue, through the console or through gameplay.

Have you considered being sneaky about it, instead of blatantly trying to free their prisoner?

This option is either bugged or simply stupid. Escape is impossible due to guards instantly attacking Benny before he enters stealth mode, even if that could be circumvented somehow they would still detect him at the first door. So Benny is not that smart after all because he immediately tries to escape without waiting for the right moment. Also the player cannot speak to Benny when sneaking so he is automatically detected by the guards as well.
So IceWolf, are you hinting some other way of freeing Benny like for example arranging someone else to free him for you (I did not find that option)?