There's a very similarly sized city on the west coast with similar population, etc.: Portland. It is a good illustration of what can help or harm cities.

Portland lacks anchors like the one put down in Pittsburgh by robber barons. Later philanthropists like Vollum of Tektronix in Portland weren't nearly as effective as Carnegie. Silicon Forest turned out to be a bit of a volatile dud compared to Silicon Valley.

Pittsburgh, on the other hand, has great universities in CMU and U Pitt. Portland's equivalents PDX State, erstwhile Oregon Graduate Institute, and OHSU never reached the heights of CMU or UPitt as they lacked the deep and broad foundation of Pittsburgh's universities.

I like both cities, but just on the basis of Shadyside-Oakland-Lawrenceville-etc. and the intellectual atmosphere there, I love Pittsburgh much more.

Disappointingly, in Portland there's no intellectual atmosphere of any sort.