I should just go to Cyrodiil
Windhelm = Freezing, racism/segregation, crumbling infrastructure (the city bears the scars of many sacks throughout history)
Riften = political corruption, poverty, thieves, open-air sewers, crumbling infrastructure (the whole town burned down in a fire decades ago and what's left was hastily put together), wooden architecture (good luck if a fire breaks out)
Markarth = political corruption, racism, terrorists, cannibals, crumbling infrastructure (it's literally just a giant ruin)
Whiterun = freezing (in the middle of a tundra), crumbling infrastructure (walls and gate in ruins), wooden architecture (good luck if a fire breaks out), furries, also giants love the open tundras outside the city so good luck
Morthal = on the edge of a vampire-infested swamp
Dawnstar = freezing
Winterhold = freezing
Villages = no walls, no fortifications of any kind, good luck
Reasons why I would live in Solitude or Falkreath
Solitude = It's described as a rich city thanks to its close connections with the Ruby Throne (and the Septims once), we see that the infrastructure of the city is well-kept and all buildings are made of stone, there's also hardly any racism, corruption, or social divide in the city, it's also the most well-defended city in the province, having high walls and an extraordinary natural advantage due to its landscape, also the climate isn't too bad
Falkreath = Good climate with lots of food to be found, it's well-defended (Skyrim did it dirty, check ESO and you will see that Falkreath is actually quite fortified), and most importantly, it's very, veeeery close to the border with Cyrodiil, and thus Civilization