I personally would love this feauture, if you RP you might be in the same situation as me. So I get attacked from, for example that racist in windhelm because im an Argonian. My character does not have it in him to kill him and make a scene because thats not how he works. Instead he hires Thugs, not to kill him, just to beat him up and teach him not to mess with Argonians or Dunmer. They go up to him and say "This is what you get for doing blalalala" or if you want them killed you hire the DB. After they have been taught the lesson next time you talk to the they will maybe be easier to persuade intimidate etc also they will drop their attitude.
Anyone think this might work?

I see no reason why you couldnt just pay up the 40 gold and assult the clown yourself and take him down to a couple millimeters of life on his health bar (as you stated you didn't want to kill him). If you can't afford it (monitarily or otherwise) then put him on your list for future payback.