Generally the more attractive the architecture looks can be a sign of how lucrative the local real estate market is. Manhattan has one of the strictest regulations on what can be built, but they still manage some pretty high profile projects. So 99% does have to do with money and how much it costs relative to how much people will actually pay.
That 657 foot tower in Cleveland will eventually cost $300 million dollars to build. The last time Detroit built something that costed over $300 million [[$412 million when adjust for 2014 inflation) was Compuware's HQ. Of course, one of the main reasons that Compuware is half the height of Cleveland's tower is because it's wider than it is tall. If Compuware was 30 stories but had the same footprint, it would have cost twice as much to build. But I'm pretty sure even then, Compuware wasn't a company capable of supporting something that expensive.
Either Detroit needs a lot of wealthy folks to want to move downtown or a very large and profitable corporation wants to move in before anything has any amount of "wow" factor to it.
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