Whiterun and Winterhold are the 2 most desired cities of Skyrim we wish to visit. Whiterun is just plain famous for its shenanigans (especially Heimskr) but some may wish to see it pre-TESV. Many fans of TES series are ACHING to see Winterhold before it got wiped out, myself included! Along with Winterhold though The College of Winterhold brings promise of practicing actual schools of magic! I would like to throw some ideas for that out there:

First off joining the college would require you choose a school among Destruction, Restoration, Alteration, and Illusion. Destruction specializes in DPS, Restoration specializes in Healing, Alteration specializes in Buffs and CC, and Illusion specializes in Debuffs and Escapes. An added perk is Destruction would be Magic Damage unless you use a Destruction Staff which changes it to match the Staff's Element. Why did I not include Conjuration? Mostly because of Sorcerer's Daedric Summoning Skill Line and Soul Magic Skill Line. Why add Restoration school when we have Restoration Staff? Because THIS Restorative Skill Line would not REQUIRE the Staff, thus providing healing options for the classes that really need it without forcing you to use the Staff.

Feel free to discuss this concept and add your own input. Either way we all wish to visit the rest of Skyrim in the 2E someday