I was lucky and passed all rolls first time I talked to her. But yeah those multiple rolls for one purpose seem like bad design to me. Set it up differently or give me one roll which reflects the same low chance of passing 4 rolls in 1. If I see that I need to roll 18 I know that this was meant to be really hard outright.
This kind of thing starts as soon as the wounded mindflayer on the ground by the way.
