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I've lived in Richmond, VA (hometown), Atlanta, GA (soulless ****hole), San Francisco (not worth the money) and Seattle (OVERRATED yuppie playground, don't bother) and for the last year have lived in my favorite city in the country, the much-maligned (especially on these forums) Steel City. You can look elsewhere to find out all of the reasons for living here, but I have an immaculate 1926 Craftsman bungalow under contract for 50k (in Observatory Hill) and I'm ready to settle down here for at least the next 30 years. Hope this helped.
Maybe parts of Cleveland? No shortage of homes for sale in this city. I live in CA but visited there not long ago. It's got a pretty nice city center, good variety of architecture and layout. Good public transit, big variety of neighborhoods. I am investigating places to escape away the southern California megalopolis in a few years. Cleveland or Dayton are two possibilities for me, but I'm not that interested in a house that has a lot of historical appeal. A small simple well built place in a decent neighborhood would be fine for me, after renting in the area for long enough to know my way around.
There are some neighborhoods in Philadelphia that seem right up your alley. Most notably, Queen Village and Northern Liberties (NoLibs) are on the cutting edge of a gentrification trend, which has attracted plenty of artists, hipsters, and "urban pioneers" such as yourself. Properties in these neighborhoods are pretty affordable and ripe for restoration -- but not, as you noted, in structural disrepair. Here are some pictures to give you an idea of the feel:
Although it doesn't meet 150M+ pop. criteria (it's SMSA is about 100M), Brunswick, GA (one hour from Savannah and Jacksonville) is full of beautiful old Victorians that are well-priced and ready for restoration. The downtown area is coming back, and I think it's a matter of time before this community is 'discovered' in a big way.
Baltimore has an extraordinary collection of old townhouses. Given the city's proximity to the wealth and jobs of the DC metro-area, I've never understood why the houses haven't been restored. It's a great old city, very walkable, lots of transportation and close to other major cities. It's a New-Urbanist's dream (with the advantage of being authentically historic).
Detroit is going through some really interesting changes right now, many young people are moving there and starting up small mom and pop businesses and the city is experiencing a renaissance of sorts. Watch this for more: http://www.youtube.com/watch?v=joMys...e=mfu_in_order (detroit lives 1 of 3)
-Pittsburgh: much of the city's north side fits my bill; in fact, based on the time I've spent there (having lived an hour outside for a year recently and getting to know the inner city pretty well), Pittsburgh might just provide the best bang for the buck for urban pioneers. The Mexican War Streets are a historic district of gorgeous rowhouses, but this section has been on the upswing for thirty years or more, so the prices are getting high. However, the neighboring Manchester area has similarly great Victorian bones (and more of them!), but its condition is not as good with only scattered restoration efforts--but it's still very affordable. Brighton Heights and Observatory Hill to the north have some very fine, large, early-20th century brick homes...you get the idea.
You're right about Pittsburgh, except it's chock-full of historic neighborhoods - maybe well over 100 different neighborhoods if you include the inner-ring suburbs - with housing at Detroit prices yet still having low suburban-like crime rates and a decent economy. Mexican War Streets is only one neighborhood, and expensive at that. I bought an Arts-and-Crafts American Four-Square with original woodwork, brand new windows, heater, electrical system and appliances for under $30K. All it needs is cosmetic remodeling. That's typical of many of the the neighborhoods.
Moving from Houston I thought I was in heaven. A house like this would easily be 10 times as much, even in a high-crime 'transitional' area. Since Pittsburgh is typically a decade or so behind the rest of the country, the natives really don't appreciate their urban housing stock yet.
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Pittsburgh!
