Look at the guiding question!
At a national convention of the American Institute of Architects' Regional and Urban Design Committee in Pittsburgh during the mid-1990's, City Planning kept asking over and over at each session: "But who do we want to attract, and what do we need to do to get them to come here?" In the final plenary session where everybody came together to summarize the previous days discussion, the City representative again repeated their plea.
A visiting architect had enough and shouted back, "You've been brow beating us with that question for three days in every session. But, you're asking the WRONG question!"
"Chattanooga, Tennessee used to be called the little Pittsburgh of the South," he said, "and they were hurt worse by the collapse of the steel industry than you were here in Pittsburgh. But they didn't ask your question. Instead, they asked, 'Who do we have here and what do we need to do to take care of us?' They took that as their guiding question. When they started answering it, people elsewhere said, 'I want to be one of them," and started moving there with their investment."
He went on, "They didn't just apply it to the people, either. They also included its culture, the physical community assets, its architecture, and infrastructure. Old buildings were re-purposed instead of being torn down. When the Department of Transportation wanted to demolish a historic bridge to build a new one, the people rose up and organized, forcing them to leave the old bridge as a pedestrian bridge when the new one was built for highway traffic." Again, he concluded, "You're asking the wrong question!"
Pittsburgh's leadership resorted and continues to resort to carnival barking tactics in their effort just to get people to poke their heads into the tent. At the same time they've roundly ignored the needs of the people who live here while providing massive public subsidies for real estate speculation (it's the people who own older existing properties who must end up paying to cover them). The smoke and mirrors may have fooled some in the media who have raved about the transformation of Pittsburgh, but it hasn't worked well. Smart people elsewhere simply weren't fooled. Most needed only ask themselves, "why would I want to become one of them and be stepped on?"
Meanwhile, as Pittsburgh continued to decline, Chattanooga shed its "Little Pittsburgh of the South" moniker. Instead, it started being called the "Little Atlanta" because of its booming economy.
So if you want a good sign of a dying city, just look at its guiding question. Whether it's explicitly asked as in Chattanooga and Pittsburgh or merely implied, it is a good indication of which direction that city is headed.