Originally Posted by Mr. Fusion
Although I don't live there anymore...Pittsburgh has one of the best urban accessibility (culture, music, food, bikes) to cost of living ratios. If you pay more than $300/month (assuming roommates) you'll be living in a sweet pad. The hills might make riding fixed a little more difficult than some other cities mentioned, but plenty of people do it. Check out the Bloomfield and Polish Hill areas, South Side if you don't mind the weekend drunks.
Pittsburgh is nice and cheap. I bought my house last year for a cool $50k... Bloomfield, three stories, 1200sq feet, wooded back yard. Mortgage is less than $500 per month, and I've got a rent paying housemate. I know people who live in my neighborhood who pay less than $150/month rent and live in decent, fairly large apartments.
Plenty of us ride fixed on the hills around here. There's a race on October 29th if you'd like to give town a proper trial run.
-brad