In my mod for Oblivion, I placed the player to rule over his own county (I called them shires in my mod). I actually didn't have time to make detailed quests or other things to make the player rule the shire, I had a deadline, so I resorted to some simple scripting to make the player be able to boss his subjects around a bit. He could arrange military reviews, influence guard patrols, boss the castle maid around a bit and arrange dinners for the nobles in the shire. These were very simple, quick things to do, but did all the difference. I later also added a functionality where the player can actually build a windmill in his area.
Bethesda could easily add such simple things to Winterhold and the Legion as well to make the player at least feel difference, feel in charge and feel that he has actually done something that carries respect in the world. Just a tip for Bethesda, because as it is now, the end of the Legion quest as well as Winterhold at least feel kind of empty.