You could always set it so there is mandatory jobs that you have to do, or be punished severely for refusing of course, and then add in extra jobs to go along with your idea. Then again, an expanded idea is that if you earn favor with the guards, you wont have to do the mandatory jobs anymore, therefor angering the other inmates who have to pick up the slack for what you no longer have to do. Perhaps one of your new jobs, to earn favor, is to keep the other inmates in line. Basically, you order them around, and make sure they do the work. I also had another idea though, involving skooma. Because it is so addicting, say that once you do it the one time, your body reacts to it, and you almost cant live without it. There could be a lot of potential with being a skooma addict. The player could suffer many negative consequences that can only be offset by the further use of skooma. That would be made even more interesting if the players condition worsened the more they take it, that their temporary cure will be no more. The player could become paranoid for example that everyone is out to get them, and so their reality shifts into madness. Interestingly enough, they could channel the daedric prince of madness while on skooma in their interactions, for one possibility. Or they could surcome to complete paranoia that everyone is out to get them, and so the character would give him/herself to very irrational behavior, and potentially even come to see hallucinations to go along with their madness. An idea along those lines hits me. At this point, the only thing keeping the player alive, is the skooma, but as they continue to take it, their condition continues to worsen. That's not to say that there isint a cure, but what if the cure was a closley guarded secret that is not obtainable by the dragonborn, or the public at all. They will only cure you of your addition once you have been arrested.