Heres an example of a quest doing this: Ok so you go meet a noble who is hiring bodyguards to guard him while he walks through town doing whatever it is he does. So your mission is you have to accompany him as he walks around town doing his daily routine. Now once hes done everything, he goes down the the slums of town. When you get there, you meet a couple other nobles (your noble's friends lets say) with their respective bodyguards who are all there for the same thing. They throw down big bags of cash, jewlery or whatnot and the nobles all bet on which hobos win the fight. Human suffering could be the game that these nobles bet on.
Now after a few hobos kill eachother, one of the dead hobo's wife shows up and starts screaming and crying. Now one of the nobles makes a remark on how [censored] of a fighter her husband was, and BAM it turns into a hobo - noble brawl.
You as the bodyguard have to now decide to either do what your contract states and protect your noble from the bums, or you can be a humanitarian, break the contract and help the hobos battle the bodyguards and nobles.
Now that would be a fun side quest, eh?
Post your opinions, and any other ideas you can think of that you can do with this supposedly advanced AI.