User blog comment:Thedoucheinthenorth/Should a city-sized Winterhold have been in Skyrim?/@comment-5423369-20121104165329

Yes I think Winterhold should had been city sized but completely ruined to give the city a personality to show that the great collapse that happened during the 4E 122 actually affected the city greatly I wanted to see collapsed buildings, ruined walls, a cemetery outside their hold because their holds hall of the dead was to over crowded from the casualties of the great collapse and this was the only way to properly honor their dead, and half the city to look like it was slowly falling into the sea of ghosts to give the city a bleak and depressing fell to it and to show its economical turmoil and that the only thing that truly survived was the The College of Winterhold.

kinda like this [|mod]

This would solve that balance of Skyrim's territories thing you were talking about and to be honest I don't really know what Winterhold's economy is based of they don't have any near by mines, their area is to barren to farm, they are extremely to far to any hold to be a trade route, they don't have docks to fish, and the only the only thing this city has is The College of Winterhold their economy could be based on this but it wouldn't be sustainable.