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Get a Slave Outfit - About the only easy part of this quest.
Get Into The Pitt - You'll be fighting raiders, wildmen, dogs, and dodging landmines to finally cross the bridge and reach The Pitt.
Work in the Steelyard - Gather up all 10 ingots for the job requirement. Or gather 100 steel ingots now and breeze through the rest of the game.
Win in The Hole - You have to win three gladiator fights to secure your freedom. Have fun.
Support/Crush the Slave Rebellion - You can either side with Ashur or Wernher to either free the slaves or stop the revolution.
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Pitt Raiders - These Pitt Raiders are a bit tougher than the wasteland variants. They are usually wearing strong armor and carrying decent weapons. You might not have to fight many, depending on your choices. Standard tactics apply though. Aim for the head or shoot away their weapon.
Wildmen - These half-feral slaves occupy a few buildings in the Steelyard and a shack by the bridge. They are lightly armed with basic weapons. If you have all your gear, then they are barely a threat. They can do a lot of damage to you when you are just wearing slave armor and using basic weapons.
Trogs - These are basically just a variant of ghoul. They are a bit quicker and more aggressive. They also ambush you as you explore the Steelyard. Be ready to turn around and quickly fight a group that drops off of the nearby building. They aren't too tough though. Even the auto axe makes pretty short work of them. Be careful of the brutes though. These tough guys take a lot of damage before they die, so you might have to rely on hit and run tactics.
Slaves - You might be fighting some slaves if you side with Ashur. They will only be armed with auto axes, so you shouldn't have any trouble with them at all. A few bullets will end any fight, especially since they usually just do suicide charges against the raider positions.
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Little Missions and Tips
Find Wild Bill - This one is simple. Once you get the mission to go to the steelyard, just talk to Milly. She'll ask you if you could look for Wild Bill in the Steelyard. You'll practically stumble across the body if you are exploring the steelyard. He's just lying dead on the stairs in the far left corner. Just examine the body and get the note to confirm his sacrifice. Remember to grab his pistol. When you go back, you can talk to Milly and tell her any of the options. You can lie and say he's alive. You can just tell her that he died. Either way she'll hand you 6 stimpaks as a reward. You can also use your speech skill to do a crazy version where you tell Milly that you found a mutilated Wild Bill in agony, who could only be mercy killed with a bunch of pistol ammo and a cinder block. She then comically passes out and drops the 6 stimpaks on the ground. They are usually thrown about during the fall though, so good luck finding them.
The real bonus is WIld Bill's Sidearm. It's a very fast, reliable, and durable .32 caliber pistol. It's surprisingly good and perfect as a backup weapon for any character.
Food - You can get free slop from Kai as a slave. It restores 25 points of health but costs you 25 rads. I personally just gather stimpaks from the steelyard, but some people might want to get as much free slop as they want. Once you get to Uptown, you can get free noddles from Lulu.
Radiation - The high radiation can be countered to a certain degree once you get to Uptown. You can get free Rad Away from Phantom if you want it.
A Dual - If you enter The Pitt in any way that leads to you being beaten by Reddup, then you can challenge him to a dual once you get to Uptown. You can kill him without any consequences with the raiders.