Actually, honestly, your map of Staunton reminds me more of San Francisco than it does New York. You know what that means? u r teh gay!!!! lololololz n00b!
Just kidding, it actually is quite awesomesauce! Have you thought about building an airport? If so, I'd study the New York/Boston/Philly airport layouts. I'd also build more than one, as it's uneconomical to have one central gynormous airport for a city the size of Staunton (see Atlanta)