Skyrim cities are terribly small, winterhold is the biggest joke, even if half the city collapsed, Why are half the remaining houses burnt down too and why would the once former capital of skyrim have only 3 actual buildings left excluding the college?
Oblivions cities at least felt like small towns, Skyrim's cities all feel like villages and they really do feel and look that way.
First, most part of winterhold fell down to the ocean.
Second, Cyrodiil is bigger and got more and bigger cities.
Skyrim is a cold harsh land, what did you [censored] expect?
Bigger cities than in Oblivion, Oblivion who was in the heart of the empire.
Yes, skyrim was the cradle of men.. WAS. Many many years ago.
And its a scaled world, you understand that? Scaled.
Places like Riverwood, Rorikstead are small [censored] "not even to be called" towns. It's they way Skyrim is. Its not Cyrodiil.
It's much more fun to be able to interact with everyone at some degree and be able to enter every house than have many peple who wont talk to you or even look at you. Or have houses you can't enter with a wall as a door.