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Can't seem to be able to get Karth to talk about the future, no matter what I do. Does anyone have any tips on how exactly they got that line of dialogue and when?

You need to at least talk to Karth after saving Gerald, then what makes the future pop up is when you pick the "You" option then they talk about trust. But make sure you talk to Lozran at the Inn about Fence, so that you have more to talk about with Karth to get to that point.