Markarth looks stunning... from the outside. But the house there seemed rather oppressive with the low ceilings. It was as if you were entombed alive. And let's not even talk about what goes on beneath that city...
Windhelm doesn't look like much. It's rather oppressive because of the Gray Quarter and all the racism. However, I really like the house there. It's huge and roomy and affordable. It has high ceilings and a huge armory. I love the wood look/feel (almost like a big log cabin).
Winterhold - nothing there, 'nuff said
Whiterun is a go to place, since it has lots of stores, a smelter and the house is conveniently near the main gates. However, I've out grown that house and don't get me started about Lydia... lol It's a quaint city, but can get boring after a while.
Falkreath - I never really considered that place. I also get lost looking for the alchemist LOL
Dawnstar is only good for the Quicksilver mine. It's a frozen place of nothing, just like Winterhold lol
Solitude has that "big city" feel and the Bard's college is pretty cool. However, I always have the feeling that everyone is rather stuck up. Plus, it has a heavy Empire presence. The house is pretty nice, but it should be for the price you pay. However, the first time around, all the bookshelves broke, so that's what I mainly remember lol It's stone on stone on stone. I prefer the warmth of wood and golden Birch trees, I prefer...
Riften - now we are getting somewhere. At first I thought Riften was just a dirty cesspool of human scum as well. However, I always liked cities near the water, like Anvil. Sure, it's a lake and not an ocean, but it's accessible and it's close. I like the wooden walkways, I like how my footfalls sound when I run across them. And I really come to like my house in Riften - Honeyside. You can sit on the porch, listen to the waves and watch a pretty sunset across the lake. There are many good people in Riften, and remember it is also the city of love, since the only Temple of Mara is home to Riften!
The Rift is a lovely place anyway. It feels like it's always fall and the colors of the trees are just so beautiful. The sun is shining most of the time and even if it's not, a light fall rain is falling, which is rather soothing. How can you not like the Rift?