In game, you might think Bravil would be a wonderful place to live, but in real life, I can imagine it would be a terrible place to live. The smelly, open-sewer canol, pickpockets on every street, mouldy, wet and leaking houses, it would be terrible!
Also, I would like to know what region people would spend the most time in, or think would be the most beautiful. In game, the Jerall Mountains are scenic, majestic mountain peaks. But in real life, it would be a deadly cold, frozen, barren winter wasteland. If you don't know the region borders, you can see them http://images.uesp.net//3/35/OB-regionMap-All.jpg.
For me? I would like to live in Chorrol, it just seems like a charming place.
What region would I think the most beautiful? I can't decide between The West Weald and The Great Forest. Both rich, forest-y farmland, with beautiful, scenic vistas.