Thanks for the honest observation.
As someone who is imbedded in Detroit, I come from an entirely different perspective in that when I stand at the corner in downtown Detroit, I feel the complete opposite of depressed and overwhelming optimism. The changes are slow, but the city was once built right, and those ingredients are still here for the next stages to begin. Economies today (of the global kind) are defined by places and the concept of "place making". You cannot replicate downtown no matter how hard you try, and it is a living definition of sense of place and place making which will act in its favor as we move along to try and reinvent ourselves.
True, a lot of the city and surrounding areas of downtown aren't very pleasant to walk around in. You get a feeling of brokenness and gaps, and some of it seems at times, intentional...like developing something for the sake of developing it even if it is less than horrid.
In terms of mentioning Pittsburgh, I've only been there a few times, and compared to Detroit, I view it as having a much more enjoyable skyline display to look at than Detroit, and even though the street/ground presence is dense and could be way more funcionable than it is, it isn't. And though I'm willing to admit, Detroit's downtown streetscape is among the worst in America (but getting better), Pittsburgh didn't seem much ahead in that regard, especially considering the built-out space and density that Detroit doesn't have. Then again, I'm not a Pittsburgh freak like I am of Detroit.
--Oh ya, awesome pic, gs!