I liked the cities in Oblivion more than Skyrim for the most part. This goes for the population, but also for the layout, and for the aesthetics. Cities in Oblivion were set up in a way that lent them personality, made them look different. I understand that all cities are essentially grown around a central hub and may not look planned out on account...well, not being planned out, but every city in Skyrim other than Solitude and Markarth looks like it was set up borderline randomly. Not in terms of function, or sense, but in terms of 'what fits here?'
For a quick example I can call to mind, the graveyard is right next to the shopping district in Windhelm (in fact, you get to it THROUGH the graveyard), which is right next to the residential district. The Inn is in the center of town, which makes it really noticeable to people coming in, but not really sensible for people looking to conduct business in the city (if we assume the cities in game are simply the representations of the cities that our computers/consoles can process, and that the capital cities aren't only a block or two wide). Additionally, cities in Oblivion all looked different. Three of the capitals in Skyrim are LITERALLY identical, despite the fact that at least the wood used to make them should be different considering that one of them is off in the frozen tundra, one is off in the swamp, and one is way the hell to the south in the temperate forests.
I also miss the number of settlements in Oblivion. I forget the names, but there were these two villages near Leyawiin that contained mostly Khajiits and Argonians, and I really liked them. They seemed like their own places, living their own lives. And there were a LOT of places like that. There are a couple settlements in Skyrim, but most of what is considered settlements are just one cabin ('Hunter's Cabin') with one or two boring ass people with boring ass dialogue. I've been hunting and fishing in these parts for years!
The ruins in Skyrim look worse. This is incomprehensible to me. Not only have graphics improved since then, but the Nords are way more into the dead than Cyrodiil was, so why do barrow tombs all look exactly the same? And you don't need to quote something about viking or celtic barrows to me, because in Skyrim, the dead have a roughly 100% chance of coming back to life at some point, AND the barrows are utterly massive. These things are way bigger than any of the cities in Skyrim. If you just cleared out all the draugr and stuff, you could fit like 3 cities population into any barrow without causing it to be crowded. The forts also look worse and get very repetitive. I guess Skyrim takes it for Dwemer Ruins, but I mean, really? And caverns...Skyrim SHOULD be better, but caves are boring and have no personality at all. They are either one room with random beasts, or they have a claw door leading to a massive ruin. There's really really really nobody who decided to live in one of those waterfall caverns? Mofo, if I got dropped into the Skyrim world according to Skyrim rules (e.g. I have at least basic competence in weapon combat), that's where the hell I'd go. Since I'm not likely to ever get picked to go rescue the Jarl's daughter from bandits, I could never buy property in any city, and I'm sure not going to slum it. If I'm homeless, I'm going to be homeless in style.
That said, I do much prefer Skyrim's interactions to Oblivion. This is both the random conversations NPCs have with each other (which always contained dialogue that made no sense), and with the player. The persuasion wheel was retarded, and there is no gentler way to say it. While I think the ability to gain affinity with them SHOULD be expanded beyond 'does some life saving favor for them,' it makes infinitely more sense than Oblivion.
