Of there is one city in the US that really should have a good transit system but doesn't, it's Milwaukee. It's the largest city in Wisconsin, has cheap land, and is right next to Chicago. It has so much potential to build out a transit system that could be interconnect with Chicago's and yet all it has is a very small streetcar loop
Louisville, Cincinnati and Columbus are also pretty high on the list of cities with a ton of transit potential and yet don't have any good transit
@when-did-this-become-difficult Yes, pretty much every transit project needs state and occasional federal funding. A city can fund part of it and would probably be able to set up a gas tax to fund construction, but state funding is still needed to start on projects