Whiterun, cheydinhal, Anvil or Bruma.

Daggerfall! Life in the big city with plenty of places to get lost and away from the maddening crowds if need be. The store selections are also great from the cheap run down weapons shops to the pawn shop one never knows what could turn up in.

Vivec, rebuilt as once was.

I've always fancied little villages, so Riverwood would do just fine! But if we're talking about cities, then I'll have to choose Whiterun. Calm and beautiful

Why Arenthia of course, doing jobs for the local guilds like the silver crescents and drinking a lot of Arenthia Red wine.

Cyrodiil - Anvil (I'd like to breathe in the scent of the Abacaen Sea every day).
Skyrim - Morthal (Nice and quiet, and good mages to protect the city)
Morrowind - Balmora (Calm, quiet city, and Ra'Vir is a cool cat )
Black Marsh - Gideon (The safest city in Argonia, if you ask me)
Elsweyr - Senchal (Sounds like being on vacation forever)
Valenwood - Falinesti (Living in a giant, animate tree? That's awesome!)
Summerset Isle - Dusk (IIRC, it's a coastal city? I like coastal cities)
Hammerfell - ??? (I don't remember any interesting coastal cities in Hammerfell. Mostly out of ignorance, because I haven't read that much lore about it, regrettably)
High Rock - Wayrest (Just sounds the most safe to me. And it's close to the Iliac Bay, so... )

And Blackreach seems pretty cool, though I'd like to find a more isolated, away-from-things-that-want-to-kill-me spot to settle in order to live there. And a good source of food, which would not mean getting within reach of robots and Falmer. Hmm...

Sentinel would also be my primary choice, having visited it in Daggerfall, it's a truly beautiful piece of gem. And hopefully it won't get destroyed like many other potential choices I would love to be still available.

Fingers crossed eh buddy? If Bethesda destroy and divide Hammerfell again in the next game I'll go Rambo mode.

Skingrad, if it hasn't been destroyed.

As of the 4th Era 201

Either

Daggerfall hopefully there isn't much conflict going on in High Rock. I would visit Wayrest too but damn corsairs made a mess of the place.

Sentinel I don't know how I'll be able to stand the heat but damn the palaces and architecture is magnificent

Whiterun since it's the city in Skyrim I visit the most. Just got to find some way of getting rid of Nazeem and Braith.

Not sure if Imperial city has recovered from the Great War yet but it be nice to visit there again. Got to be on guard against Thalmor activity though.

Yea about that... you'd have better luck with Daggerfall.

The Imperial City. It'd be beautiful even if it was still damaged by war, and I daresay it's still the busiest city in Tamriel. Of course, I'd flee as soon as there's a hint of war - likely to Raven Rock on Solstheim.

The first one to get optical fibre broadband will get my vote.

Winterhold everywhere else is to warm.