Fnv how little we know

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I tried the speech method where he will come and shoot with you and the other one where he just passes you a gun.

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So I have followed the walk through, and at the part where Cachino and you are supposed to go have a meeting with the bosses. I am on The House Always Wins IV - (deal with omertas) and which coincides with How Little We Know. Long story short: I am really stuck, Cachino seems to be bugged, tried 4 different ways through and still bugged