It's not in as bad shape as Detroit, but Blue State and Blue (corrupt) local governance have driven most of the jobs away - along with vast numbers of middle- and working-class people. (The prosperous fled in the 50s and 60s.) Therefore, there is no "housing shortage." Housing is cheap, but they will kill you with the property taxes. Thus the old city has no vitality or appeal whatsoever except to urban explorers like us. Death spiral.
What does a pilot do in a death spiral?
The solution is not to bulldoze the city. It's to bulldoze the government. However, at this point the government is basically in the control of government unions and welfare recipients, all feeding on the dry bones of the cadaver. Thus, despite its amenities and opportunities, basically politically hopeless. It's sad.
If they appointed me Dictator of Bridgeport for a few years, I could begin to fix it. Change is good! The first thing I would do is to create a citywide enterprise zone with no corporate or business taxes. Second, I would cut property taxes in half. Might be tough going for a couple of years until markets react, and bankruptcy might have to happen because sometimes you need a fresh start. Third, I would eliminate all government housing. Rents are so low there, anybody can pay them on a welfare or disability check. Fourth, I would make government unions illegal. Fifth, I would prosecute the local Mob with vengeance, no mercy. Everybody knows who they are, and people claim they are in bed with the unions. Sixth, I would eliminate all zoning regulations. Seventh, I would make all schools charter schools - no government-controlled schools. Eighth, a cop or guard on every block, with stop-and-frisk. Well, I could go on and on, but the general idea would be to return such a city to the policies which existed when it became a thriving city, before the socialists, planners, and taxers took over when they realized they could tax and plan the place to death.
It would be an interesting experiment. If it failed (but how could it be worse?), I'd take the fall.
This row of old buildings appeared fully-occupied by Hispanic immigrants, neat, clean, and pleasant but nowhere to go except the abundant old churches, and no street life.
Government policies can kill cities. From Mead's New York No Longer Skyscraper King:
...those worried about the future of what George Washington once called the “seat of empire” should take heart. New York has a plan: more regulations, more taxes, more spending, raising the minimum wage, and raising transit prices. And we’re already seeing the results: a vanishing middle class, mass exodus of businesses, and an unhealthy dependency on a rickety financial industry.
Sounds like a recipe for success.
The northern states had wanted NYC as capitol. The compromise was reached on a swamp in Virginia.