Not sure about other older cities on the east coast, but the problem you describe is a good description of older parts of much of my city.
We have a lot of dense 30’ city lots with no parking, and narrow residential streets not wide enough for parking on both sides. If people park legally, larger vehicles like emergency vehicles cannot pass. So most people park on the sidewalks in residential neighborhoods and it is tolerated. This blocks sidewalks for pedestrians and the disabled, and the sidewalk crumble, look awful, and are a hazard to walk on when cars aren’t parked on them.
Back when the neighborhood was built, there was a robust transit system and everyone worked and shopped in the city center. But now, we have shopping malls, suburbs, and office parks. No longer can a person shop and work exclusively in the city center. It’s too spread out.