Can you point out a city that built up and is affordable (with a good economy also)?

Here is a random 10-year old condo for $255k: http://www.trulia.com/property/3201711637-222-N-Columbus-Dr-...

Here is an older, further-out one for less than half that: http://www.trulia.com/property/3193730688-3950-N-Lake-Shore-... (still in a decent neighborhood and near a 24-hour rapid transit line)

Here is a large 3-bedroom for $485,000: http://www.trulia.com/property/3197384352-212-W-Washington-S...

Here is a large 3-bedroom, futher out, for $450k in a newly-built brick walkup: http://www.trulia.com/property/3027918821-2550-W-Logan-Blvd-...

There are a lot of variations on similar themes.

Chicago's economy isn't San Francisco's, or New York's, and it doesn't have many exciting software jobs or world-class outdoor recreation. But it is still a big city with big-city opportunities and many well-paying jobs. And it clearly demonstrates that a sufficient housing stock guarantees no building type, even skyscrapers, are inherently tied to high prices. Just as San Francisco's predicament demonstrates that keeping old buildings in place doesn't hold down prices.

From personal experience, at least, supply is _not_ an issue in Tokyo. You can go to a real estate agent and go see like 4 or 5 places in a day and take it almost immediately.

This is compared to (second hand stories) of apartments in Paris where you have 10 people show up to look at 1 apartment and it's a crapshoot whether you can get it.