I'm from NYC, and there's not much about Bridgeport that feels distinctly NY to me. It's one of the reasons why I never warmed up to it and started building my own worlds. Parts of it kinda sorta feel like NYC but not at the same time. For instance, the bridge is brown and made of brick like The Brooklyn Bridge but it doesn't look like it at the same time.
I think that it was more inspired by open worlds from other video games but then threw in a mixture of real cities to create its own signature look. Aspects of both Bridgeport and Starlight Shores feel like they were using San Andreas as a template.
