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Hmmmm this sounds like a bug to me. I’m also in survival and Trudy is alive. I doubt KG intended to railroad you into killing Trudy, and offering no heads up beforehand that you’ll have a quest that can’t be completed based on a choice you made many hours earlier.
Edit: looking at the quest more closely, seems like an issue tied to vanilla mechanics. The best solution would seem to be for this quest to trigger at the same time as the Walden Pond quest, as it is unlikely that the player will have reached drumlin by that point (assuming it’s a new play through of course).
Just wanted to say this is still a problem 3 years later. The quest gets stuck when you talk to Trudy, even though Wolfgang asks you to in his dialogue. I had to dig to find this post to figure out a solution.
Thank you to those who posted ways to advance or complete the quest with the console. It's a shame that's necessary.
Can we please report this as a bug? I know we're not allowed to report it ourselves and a moderator is required to move the post to a bug report.