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If you just click on the persons character portrait in the village menu screen (you can see the name of the guy you need in your journal), it'll transport you and the guy to the person and start the dialogue immediately.

I'm pretty sure if you kill the surrounding forest bandit parties, it lowers the number inside the hideout! worked for me with the sea raiders! (And then promptly get the infinite loading screen at their hideout)

I get decimated as well. However, When I was trying to figure out how I was going to take on 30 sea raiders with 8 guys i discovered if you kill as many surrounding parties as you ca, it seems to cause the garrisoned troops in the hideout to start leaving? So If you kill any forest bandits around I think that'll help.