Well my characters are for the most part the goodie two shoes, but I have made characters for the more bad intentions just to see what the quest of the same like were about. My characters that were made for the purpose of good doing (like how I prefer to do things myself) never touched the stealing and hurting of innocents. As far as the dark-side characters the only reason there was ever more then one was save-game corruption or having to reinstall from the bottom up.
The sole reason the dark-side characters existed was to see the story, and that was the type and kind of character required and usually only done once.
If there was a way to add a kind of open faction wars with repeat raiding of towns and settlements with generic respawning npc's merchants and guards just like world of warcraft (at least that's where I first experienced it) I'd be all over it. Raiding towns and smaller settlements was rather fun
but with the situation with both morrowind and oblivion if you kill the merchants and guards only the guards come back and you get a universal bounty vs if you were raiding an enemy nation you wouldn't get into trouble with the home guards. So its better just to leave the townsfolk alone and not make trouble so you can still exist with out repeat guard attacks and really empty towns.
Something else I've heard about reading on other games there was another game where they had some similar things to elderscrolls but some interesting additions. One was quests to help take control of a town by opening the gate allowing say orcs or marauders to take the town, or helping defend the whole town from the two said forces. Then after if you had helped the invaders a force of soldiers would come to try and retake it. Also your character would be only remembered by npc's for what they last saw you doing. Like if you helped save a village the villgers would remember you for that but in the next settlement if you stole or raided the npc you stole from or villagers you raided resources from would hate you for said actions. So no universal champion of cyrodiil etc title for that game you reap what you sow for every action.
If I could remember the games title I'd post it for reference I guess I'll just so a search latter and add it in as an after thought among other things it was a living world, stuff didn't only happen when the player was in the same location so the raids and town take overs so it would be in control of one group when you last visited and another the next. Its not mount and blade though it has some of the same concepts it was played from a lone adventurer perspective.