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You're either on one side or the other in the fight. Talk to Bobbi Meet Bobbi in Diamond City Get Mel Out of Jail Recruit Mel Meet the gang in the Dig Dig to the Strongroom Meet with. Don't like Bobbi and do like Hancock? If you side with Fahrenheit, you get to kill Bobbi right then and score points with Hancock.
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The player character is subsequently given the choice to persuade Bobbi to leave and surrender, kill all the. You'll also still get the Ashmaker, because Fahrenheit is nice like that.The room is filled with the mayor's henchmen. You’ll need high Charisma to make this work, but you avoid a fight. Speak to Fahrenheit after finishing Bobbi and she’ll give you the Ashmaker. Shotguns and melee attacks also work really well.
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Bobbi likes to hide in closed spaces, and you can smoke her out fairly easily with explosives. She’s a more potent opponent than she looks and can take lots of abuse, but it’s an easier fight than going agains Fahrenheit. In this case you’ll have a solo duel against Bobbi. Pop open the Strongroom (the train car) and Bobbi will give you your cut. Once you kill Fahrenheit you can steal Hancock’s Strongroom Key and her Minigun, the Ashmaker, from her body. Take cover and let your companions draw her fire. The Triggermen are no big deal - they’re both in defence-light Hazmat Suits, and easy to kill - but Fahrenheit has a Minigun, and she’ll use it to spray you with bullets from above. This will put you in a fight against Fahrenheit and two of her cronies. Stealth kills are feasible in here if you want a quieter approach, but the moment you botch your stealth the whole place will come down on your head. This will take a while, as they’re well-equipped and numerous, but it’s quite possible.
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