The US's objectives have rarely including a traditional win, so that isn't a useful think to ask about.

I don't know where your US rail system comparison comes from, but the US rail system is not stuck in the 1950s, the US rail system is the best in the world and has innovated. You might be thinking about passenger rail, but that is small subset of rail and not useful for most US needs.

Pan American highway or Pan American - these are feel good ideas of questionable benefit. They would sound good on paper, but they would not be useful for much: flying is faster (and probably cheaper) for things that need speed, while the nearby ocean is much cheaper for things that don't need speed.