I can come up with other cases, but there is a lot of other technology that needs to be worked on before we are ready to build generation ships heading to other star systems.
https://www.forbes.com/sites/ericmack/2015/07/19/trillion-do...
"Even today". There is an opinion that payloads are so expensive because the launchers are expensive. I.e., you can't send replacements easily, because a launch is expensive, so you have to design the payload so that it wouldn't break, and last 9-s of reliability cost additional 0-s in price.
In other words, if launchers would become cheaper, that would encourage sending more payloads which isn't designed to be as reliable and serve as long. If something happens, just send a replacement. The issue of space junk comes to mind, but if launches are cheaper you can include into the launched mass the active means of dealing with space junk, like fuel for deorbiting.
As for asteroid mining, Caterpillar was considering lunar base operation equipment on a previous iteration (G.W.Bush program). You probably right, they'd present a hefty bill, but I somehow doubt they'd offer something truly innovative. Maybe with new scrappy startups we can drastically slash those non-launch costs - then we'll come back again to the question of launch prices.
Over time asteroid/moon mining is inevitable. Technology will develop (costs fall), and we'll exhaust the mineral supply of Earth (prices increase). I'm sure, among many other types of organizations, scrappy startups will help us get there.
The problem is that nearby asteroids tend to be dry since they're being warmed by the Sun as much as Earth is and lack Earth's gravity well, ozone layer, and magnetic field. You want to go to Jupiter's trojans or so, or maybe just Ceres if you're willing to deal with its gravity well and dig a bit. For Jupiter's orbit you're looking at 3,300 m/s plus escape. Still a lot less than getting to orbit and you can use an ion drive but hardly trivial.