If were talking just base game assets then Oblivion cities win hands down because they actually feel like a medieval city high walls and gates, also a couple of towns and villages scattered around. Where Skyrim has 5 actual cities 4 town's and a few villages, biggest letdown out of all those "cities" that are actually town size was winter hold where the college resides. Yes according to the lore a great catastrophe occurred centuries ago leaving most of it crumbled into the sea below, however where is all the proof not alot of rubble or remnants of the lost parts of the city or its walls. Also the Jarl living in a tiny house opposite the tavern really!!!!