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Questions:
- Are you running any mods?
- Is the quest marker working?
- Are you doing the bounties within the timespan of an in-game week?
Anyway it takes about 3 days for indoor cells to respawn so you can wait around if you want but don't quote me on that.
i got the quest and tried it the first time and the leader just lied there after i killed him. i waited about a week for everything to respawn and tried it again and this time the maurder was there. i killed him and the nothing happened. i waited another week for everything to respawn and tried it again. i got the bandit leader but the quest marker was not on him. i killed him and the quest did not finish once again.
So the cell did reset and the quest marker still points that your target is in Uttering Hills and even you go there, the arrow is pointing at an empty space? This complicates things...
Have you completed that Thief Guild quest relating to this? You'll know what I'm talking about if you've done it.
Anyway you can try the console commands but save first before you do.
http://www.uesp.net/wiki/Skyrim:Bounty:_Bandit_Boss#Bugs
setstage BQ01 stage 100