I triggered it on my first play through and haven't triggered it since. I think it's tied to approval and long rests. If you raise his approval too high before triggering the scene, you're locked out. It could definitely use a tune up.
Ahhh.. His rating is high.. I managed to get the discussion about how his Problem happened etc.. but he still isn't asking for magic items.. Oh well.. we can't finish his quest while still in act 1 anyway.. I will try not to let him get too happy with me too fast next time.. Hope Larian gets it "fixed" so it will start anyway.. Thanks
