I don't know about D.C. or Detroit, but here is my instance of the class "Pittsburgh":
85 year 2000 sq. ft brick house on 1/4 acre. 4 BR, 2 ba, 2 car garage. Totally gutted and modernized. 3 miles from downtown, 1 mile from Oakland (Carnegie-Mellon, Pitt, Carnegie Museum/Library, Schenley Park). Walkability index 92. Within one hour flying and 8 hours driving of 50% of the U.S. population. $160K. Same house in Miami: $500K. Same house in California: 7 figures + first born.
4 distinct seasons, but some people still don't like the weather. I prefer these thoughts:
"Everybody complains about the weather but no one does anything about it." - Mark Twain
(Looking at gray sky) "What a beautiful day, Herman!" - Lily Munster
I have the bottom floor. 3 bedrooms. 3 roommates. $1200/month rent, so I'm paying $300/month. (my girlfriend and I share a room.) I live in one of the more affluent neighborhoods in town. Yep. It's that cheap.
20 minutes walk from CMU, 30 from Pitt. Buses come either one block or 4 blocks away. CMU shuttle goes _past my house_. One block away: 4 bars. A restaurant. Two coffee shops. A bunch of other junk. A Japanese grocery store two blocks away, regular groceries about 5, a Whole Foods about 8. My two neighbors on either side are families.
I don't like the weather. It's too rainy and spring and fall are far too short (some of my friends call fall/spring "poorly dithered winter and summer", since it tends to just jump back and forth between cold and hot for a week or two).
A house like that isn't 7 figures in California - it would definitely be above 500k but it wouldn't break a million in a lot of places near SF, LA, or SD.
It's a shame about the grey, overcast winters and the muggy summers though. I went to college there for four years, and it's a great city, I just couldn't stand the weather.
Looking at the worldwide list it seems like access to healthcare plays a really strong part... which I guess makes sense if you're calling your metric "Livability"
Pittsburgh, seriously? Between the small, crowded, pothole-filled roads and buses which are never on time, it's impossible for me to get anywhere around here. The Steelers football fanaticism drives me insane and the weather is terrible. I absolutely cannot wait to move away from here next year; the city's only redeeming quality in my eyes is the plethora of universities.
Pittsburgh can be a bit of a shock for the San Francisco set though. There are comparatively few of what I'll call "post-hippie" establishments here. They're around, don't get me wrong, but not like in the liberal bastions of the West coast (Seattle, Portland, San Francisco, etc.)
One of the most celebrated places to eat around here, Primanti Bros., sells giant greasy, meaty sandwiches with fries and coleslaw inside. Froyo places have just shown up recently!
By some criteria, I'm sure. But if you like Broadway shows, it's not the best choice. And while there's a river or two, the surfing's not all that good. I suspect there are better places weather-wise, too.
And I might be interested in some of those criteria at some point, but it's like some article that said it was great to retire in Fayetteville, Ark...
Pittsburgh's 1985 win (in the middle of the steel industry collapse) prompted a lengthy screed about how cumulative ratings are assembled from a UW psychology prof:
http://www.briem.com/files/Loftus1985.pdf
Pittsburgh keeps winning most livable city awards today for the same reasons it won in 1985: it's a city that rates good or very good in everything and bad in almost nothing.