*spoilers below*
This quest (from what ive heard and experienced) is very broken. It starts by having to side with the powder gangers from the start at goodsprings or you'll be vilified with them. The only option to fix this is to stand there and not shoot any of them during the fight in Goodsprings and hope that you only get shunned. This isnt really why the quest is bugged though, it's just annoying.
If you plan to keep the Powdergangers in charge of the prison and side with them, then the quest plays out fine. If you choose to help the NCR take over the prison, thats where things turn ugly. First, you can't activate this quest to side with the NCR unless you talk to Eddie (which is why being vilified with them from the very start is a problem). It's impossible to speak to Eddie if you're vilified even with a constume (that should answer your question). This, imo, is a huge design flaw, but let's move past it.
Once you actually take back the prison (for the NCR), and if you've completed the Bison hotel question in Primm, the npc you're supposed to return to is gone. You'll eventually get a message saying he's dead at some point during your game because he just decided to up and leave and wander around until he dies. This screws up whatever he's supposed to do in the story. Theres also the issue that no matter how you resolve this quest, radio new vegas will always say the raid on the prison failed (even with sgt lee standing right in the middle of the prison).
It really svcks if you're trying to do a full ncr run and I hope it gets patched soon. I havent found any way around it though or a way to fix vilified rep with PG which you (for some ungodly reason) get within the first 5 quests.