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I usually refuse the ones requiring soul gems as you always suffer a profit loss from this skinflint. His quests always alternate between item pick ups and soul gems wanted. I learnt to save my game every time before checking what he wanted, as I had the same problem with Sabine.
discussion from 2013, but if anybody looks for fix in this year it may help :) ). I'm sorry for my english I'm not native speaker.
Follow her around until she walks up the stairs and next to the exit, interact with her when she is next to the door (I did a quicksave as she was walking up the stairs towards the door just incase), then go through the door while she's telling you you shouldn't be there. She'll travel through the door with you, then interact again to talk to her properly now you're both outside.