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Your particular issue with this scenario comes if you bring Paul along for the ambush. If Paul is there, you can't shoot Cooke at all because they're meant to have a conversation after Trish dies and then you either let him keep half the drugs (everything at the ambush deal) after which he becomes the bar owner in Diamond City and a wealthy citizen (although that ending is also bugged because he won't leave Cooke's house after that).
You can only save Trish if you don't bring Paul, but then Paul won't be the owner of the bar in Diamond City.
If you let Trish go, she informs the boss about you. (She lies to you about not saying anything).
All in all, until the unofficial patches roll out or if Bethesda decides to fix gameplay issues, you have only two choices :
-Bring Paul, let Trish die, decide what to do with the stash.
-Don't bring Paul, kill Cooke, keep the stash > Paul is a nobody in Diamond City.
I personally like having Paul becoming a wealthy citizen and the bar owner.
Also PRO TIP : DO MANUAL SAVES OFTEN. Not quicksaves, not autosaves - manual saves.
I can't bring Paul. I can only inform him that I've dealt with Cooke.
I though it was a real d.ck move when Cooke proceeded to kill Trish even though she had told everything. Didn't think killing him would mess everything up like that.
I just finished the quest though. I think it finished as if Paul was there and I decided to keep the stash to myself.
You're right. I should do manual saves a lot more often!
Even though I was able to finish Diamond City Blues, Colette does not spawn and Darcy doesn't give you the photo that initiates the next quest. I was able to start the next quest through console commands and finished it. However, I don't see a way to get Colette to spawn.
Why didn't Bethesda make Cooke unkillable in that part of the quest? I've spent 3 hours trying to figure this stuff out!