When I played Oblivion on the Xbox 360, Skingrad was my home base. At that time my character had almost 1 million gold and I hoarded all the rare items in the game. Skingrad seemed like a great, expansive place to store all my goods, and I think it was the most expensive home in the game too.
I wanted to like the house in Anvil, but it always stayed kinda creepy after the haunting, and the ectoplasm never disappeared, which I didn't like.
If I were to play Oblivion again, I would probably live in Leyawiin. I always liked the look of the houses, they're very cozy and colorful looking. Second choice would be Bravil. It's a slum but I like the look of that town too. It has it's own charm.