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According to the Fallout Wiki, I need 5 "points" to get him to talk about Bittersprings and start his quest.
When torturing the captured POW Silus at Camp McCarran, if he dies during the torture: +1. During the mission 'I Put a Spell on You', if you kill the spy: +1, if you disarm the monorail bomb: +1. Killing the Legion leader: +2. During the side quest Booted, rescuing the hostaged Powder Gangers: +2 When first arriving in Nipton, killing Vulpes Inculta: +1 During the side quest Back in Your Own Backyard, if you kill the hostages: +1. If you save them: +2. During the side quest Eye for an Eye, eradicate the Legion for: +2. After killing Aurelius of Phoenix in Cottonwood Cove.
I should have nine points total out of all of those. Why won't he talk to me about the damn quest?