For me? The "city" of Winterhold. It's a city, but it's comprised of one house, one inn, one shop, and the longhouse. A lot of rubble homes that look exactly alike too.
Let's start with the lore behind its condition --which is solid, to be sure.
The city has fallen on hard times, and was wrecked by a cataclysmic event which caused much of the place to fall into the ocean. Okay, I can handle that. So... why isn't there any building rubble at the bottom of the cliffs? The only object accounted for were the pieces that fell from the bridge. Rubble doesn't float, it's not going to be miles out. I was irked how little was accounted for below.
Then, the reality of the situation. It happened 80 years ago, according to lore. As Nord tradition states in Skyrim, nobody is allowed to rebuild anything. Just live in ruins, right? No attempt should be made to rebuild the wooden homes after 80 years of wreckage. The economy truly stunk after the Great War I suppose. This aside, Winterhold remains a town about the size of Karthwasten, which isn't saying much.
How does the town manage an entire hold? Where do the guards sleep? I feel like Winterhold had a great shot with the lore, but didn't match it well with design. No problems with the College, no problem of ugly or neatness. I'm just a bit disappointed in the practicality of the final result.
Wait. Nordic tradition says you aren't able to rebuild anything? As in, that's in an ingame book?
That's completely menally deficient of the developers. The Nords aren't nomads. They form more or less permanent settlements. Farmers would be completely screwed over without the ability to do maintenance..
What I don't get is that both Dawnstar and Winterhold are IDEALLY placed to be a sea port, and neither of them is. Dawnstar at least has a dock. You'd think the military or the merchants would take advantage.
So you'd think that it would be advantageous for the nords to rebuild the town. It certainly doesn't make sense to me that they wouldn't rebuild the town. I live in NZ - in the 80 years between the 1st world war and the 90s, I'm pretty sure our population quadrupled. 80 years before that, there were no european settlers whatsoever, and the country was mainly dense native bush. So in 80 years they cleared lots of the bush to make room for themselves and livestock, and end up with a population of 1.2 million. In the next 80 years it doubled twice. Winterhold's situation doesn't make any sense.
Then you consider cities like London, which had the houses of 70,000 of the 80,000 inhabitants destroyed due to a disaster and then were rebuilt.
To me, the current situation surrounding Winterhold seems like laziness on behalf of the developers. It makes no sense for a great city, which is flourishing politically and economically, to be more or less completely abandoned by its occupants because of a relatively small natural disaster. It actually seems more like the developers had an attitude along the lines of "Well. The cities are this big, that's big enough. Let's scrap Winterhold, say half of it fell off a cliff, and just leave the mages college there".
Its stupid because a college the size of the mages college would require a whole lot of support services - like food, water, servants, clothing, carpenters, printing presses and so on just to keep the place running, so the town of winterhold should definitely have more than just a handful of buildings. It really should be a huge city.
Oh yeah. Another annoyance for me is the name of the East Empire Company. Where's the West Empire Company? They've made the distinction, after all.