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.

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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.