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I've given him the Dragon arrow in my first visit. And he should kill the Dragon in the morning...
I had 2 Dragon arrows (2 x Quest) I used the other one trying to kill him (dragon) directly but in vain. I can always purchase a new dragon arrow and visit Torin again and again give it to him.
As for the money trick I have my Rogue/Ninja/Monk doing fletchery in his spare time with the bushido arrow (the one that pays the big bucks).
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