So, I decided the first thing I would share are some of the maps that I've been working on. Really shitty, but maps all the same. The first one is a sketchy map of Winterhold in 3E 390, long before its collapse. At this time, Winterhold was at the height of its power, with its walls stretching across the bay.
As you can see, Winterhold has nine districts, and is centered around the College, as well as Dunmeri culture. Winterhold was one of the more multicultural Skyrim cities back then (it's not now.) After the Great Collapse, only the western portions of the market district remained intact, (as well of the College of course.)