As it turns out, when you don't fund crucial public services, they don't work very well. It's a fun cycle: The DC Metro has no dedicated source of funding nor particularly united constituency, so it gets shortchanged come funding time. Inevitably, the lack of funds degrade service and lead to failures. This makes the Metro less pleasant, driving people away, serving as an argument that government can't do anything right, and giving fuel to those who say that we should reinvest in more roads and private transportation infrastructure. As Ryan Avent pointed out, here's the result: This year, the government will allot $1.4 billion in federal spending for transit, and $42 billion in federal spending for highways. Sure is a mystery why our public transit systems don't work better.
I also think Ryan's right to say that "while residents of cities with good transit systems understand how popular and helpful those systems are, residents of other places–that is, most of the country–still view transit as a bit utopian and inherently unworkable given population densities." Subways are such an engineering marvel that it's almost impossible for me to believe that they really exist, or that we could build more of them. But they do, and we can.
I think a bigger problem is that the sorts of public transportation that are beloved as an alternative to cars -- namely, systems that don't use roads, and thus evade traffic -- need to hit a critical mass of lines, stops, and, stations before they become a real useful alternative. Building that sort of infrastructure takes time, and our politics doesn't tend to like solutions that won't solve anything before the next few elections end.