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Finding The Pitt
This is a simple startup. You'll get a notification about a new broadcast coming in across the wasteland. The source is pretty far away. You'll need to go to the most northern part of the map to find the radio beacon. A man called Wernher is by the marked spot fighting a few Pitt raiders. Help him out and then talk to him. He'll explain the slaves' plight in The Pitt and direct you to the tunnel for you next mission.
Just go west to the marked location. There's a slave camp by the tunnel entrance. You need to get a slave outfit before Wernher will take you to The Pitt. You can just buy the 3 slaves from them for 600 caps total. You can try to pickpocket the key off of Ramsey and sneak into the cage. You could also pick the lock if you have 100 points in Lockpick. You could also just shoot the four guards and loot the key. That's probably the best option.
Also, if you have already killed Eulogy Jones and cleared out Paradise Falls, then they'll recognize you and turn hostile as soon as you start talking to them. Might as well go in guns blazing in that situation. Either way, kill them all and then sleep in the bed to heal. Open the slave pen. You can scare Prosper into giving you his outfit or grab a slave outfit off of the dead slave. Wernher shows up as the edge of the camp once you get the outfit. Talk to him and walk into the tunnel. Activate the mine car to travel to The Pitt.
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Getting into The Pitt
You've still got a ways to go before you get into The Pitt. The Pitt Raiders have a checkpoint set up watching for Wernher. Hang back and watch Wernher talk to them for a minute. He'll eventually open fire on the raiders at the checkpoint. His skill depends on your level. At level 11, he was still able to clear out all of the raiders with his scoped magnum. He barely took any damage. You can be pretty safe in just hanging back for this one. Loot the bodies and wait until he walks up to the gate and opens it. Go ahead and ask him about sneaking in a weapon. You can then get a concealed gun or knife. It won't help much, but there's no reason to not get one.
Walk up the path and watch the building to the left. It has several Wildmen in it, so just avoid it. The loot isn't that good and you're going to lose all your stuff in a second anyway. Get onto the bridge and be very careful. There are lots of mines on the bridge and some traps on the side walkways. Jump on the cars to take either of the zigzag paths. Get onto the sidewalk and then back onto the main path to get around the overturned trucks. Remember to save often, since mistakes are quite deadly here.
Watch out for the two dogs fighting the mole rat inside the truck. A minefield isn't a good place to fight. Kill them while you're on the side path, jump over the rail, and keep disarming the mines. Watch out for a big overturned truck. The radioactive barrels it spilled are quite dangerous to you. Avoid them by sticking to the left and going over the rubble pile. The last difficulty is the sniper on the top of the bridge. He's a real pain to kill and he seems to shoot, even if you are in a slave outfit without a weapon. If you can't sneak past him, then kill him and move off of the bridge. Wait for the slaves to get blown up in the minefield. The explosions are scripted and happen whether there are mines there or not, so hang back. Walk up to the gate.
You have a few options. You can just follow Wernher's plan and wear the slave outfit. They'll let you in and take your stuff. You can then walk over and look for Midea's house. You don't have to do this though. You can just walk up in your usual armor and ask for a job in their army. They'll ambush you as you enter downtown and knock you out. You can also kill the entrance guards to be ambushed as you walk downtown. It doesn't really matter.