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Detroit is probably the best right now considering the categories you listed, but I suspect Baltimore has the brightest future. The proximity to Washington (and other East Coast cities), being situated on the Eastern Seabord, the iconic harbor settting, being located in a wealthier state, and especially the colonial history and architectute all provide the basic structure for prosperity and growth. Detroit doesn't have this, and St. Louis only has history. I suspect St. Louis will continue to decline, Detroit will continue to rise very slowly, and Baltimore will at some point just explode.
CoL————— Detroit
Nightlife——— Baltimore
Food————— Baltimore
Safety/Crime—- St Louis
Transit————— Baltimore
Shopping/Entertainment/Events— Tie
Skyline—- Baltimore
Downtown Vibrancy— Baltimore
Local Culture— all have a uniqueness so tie
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