Let me try to address this from a slightly different tangent, with examples.
For any number of the projects many on this board now consider urban screw-ups, there were alternatives -- probably viable alternatives -- that were proposed. The proposers, however, didn't belong to the club, and no matter how attractive (and I dare say "visionary") their proposals appeared, they were ultimately marginalized. (You would often hear them referred to as "mavericks," a code word that always meant they'd at best be patted on the head, or at worst sued for exercising their rights as citizens.)
Take the Gateway Mall. Donn Lipton owned the buildings (Buder, International, Title Guaranty, RIP) and presented a plan to keep those building, blow away some of the clunkier infill, and build new ones. But Donn never had lunch at the Bogey Club on Monday. The buildings were taken by eminent domain, and rather than having a dense downtown interior corridor with a bit of green space, we got, well... (Not to mention the loss of probably more than 100 entrepreneurial-style service business that occupied those buildings.)
Steve once wrote a very good then-and now commentary.
Anybody remember the Children's Building? It's now that fine surface lot immediately across from the Kielvis Trade Center. And that one had an actually-connected potential developer, Charlie Drury.
On a more general note, I can probably dig out any number of clips that pointed out that if Union Station's business model required it to charge for parking, it would fail.
Anyway, point being: We've never had a shortage of ideas; we have had, and continue to have, a combination of gross lack of leadership combined with virtually nil entrepreneurial spirit (which is equal to almost total risk aversion).
And this is why I'm skeptical, or some would (wrongly) say cynical, or just plain sad about the until-now reaction to City To River. (An idea, by the way, that I can prove I've been advocating for almost a decade.) The concept promoted by City To River has crystal-clear upside potential. Anyone with even a raindrop of vision and imagination can see that.
And yet, it's the Alexes and Ricks who are spearheading the effort. NOT ONE local "leader" is "leading." And don't give me this "leaders only support sure things" argument. Luther Ely Smith didn't have a sure thing. Turn old buildings, some of them in really bad disrepair, into hotels? That clearly wasn't a sure thing, but Charles Drury pulled it off multiple times. Craig Heller took a huge risk and achieved proof of concept, but then he got marginalized.
I'd like to believe that a few bright folks with visionary ideas can break through -- Bonasch Boulevard, anyone? -- but the local culture has never allowed that, and nothing that has occured recently has offered any evidence that things are going to change. Should the next generation just give up? Not at all. But you really are going to have to infiltrate that culture to become the next Luther Ely Smiths.