I get your point about how our existing transportation system is functional. I mean, it's not, but it's functional enough that people and policymakers can point to it and claim that it's good enough. We can't point to all of the trips that aren't happening because our system is so godawful exactly because they're not happening.
I just think of Amtrak's Borealis route from Minneapolis to Chicago. It's not terribly convenient (2 trains a day), nor that fast (7½ hours), nor all that cheap (close to $50), and it has blown ridership projections completely out of the water. A lot of people really want to take the train, and I understand, because the alternatives (driving or flying) are so much worse.
I have plenty of friends who'd love a train to Chicago. The Illinois Central route is still in use for freight. But Wisconsin just can't get it together to offer passenger service. Beyond NIMBYs, as we saw in the campaign for governor in 2010, rail has become a political identity issue, coded as Democratic, so Republicans are reflexively against it. As well, it's a racist dog-whistle, as seen in the bizarro claims that a train would bring Chicago crime to the city.