In case of the Trapped Man, you need to rescue him a certain way:
- First enter the building by helping the Flaming Fist with the main door or go to the right wing of the building, where the barrel is blocking the doorway, then jump to the second floor and there will be a locked door.
- Get the woman.
- Go to Benryn, but not trough the door on the right. First, destroy the door on the left, help him and tell him to follow you.
- You need to get out of the building trough the main entrance (the issue I had is that I lead him trough the door on the balcony and it didn't count as "saving him").
To finish the quest:
- Talk to Benryn.
- Find his wife's body (left wing of the inn, second floor) and tell him where she is.
- Then talk with the wife using "Speak with the dead" spell. She will tell you where Brenryn's sister's ring is (if you don't have the amulet or the scroll of Speak with the dead: the ring in question is in the barn, in a stack of hay)
- Give him the ring. An done. Wyll stops complaining.
So, looks like at the moment, going left and saving him that way doesn't count as success, even if you talk to the wife and get him the ring. And the same conversation with Wyll happens if you save him "the right way", but don't get him the ring. That's in my case, anyway.
[Update]: Nope, the quest is done but after 2 long rests Wyll had his "we did nothing" complaint.
