We aren't going to do it. Not by the millions, and probably not even in the thousands.
This is an excellent survival strategy.
(By "pretty well" I mean that tribal civil wars and familial strife make life damned miserable as groups hit Dunbar's Number and have to divide over and over)
Some very wealthy and intelligent people are going to go broke and insane as a result.
We will get a desolate moon base and a ghost town of a Mars colony as a result.
Our desire to explore all niches is not met by the masochism required to inhabit them all. We don't raise our children in intolerable places.
The very drives discussed here are waning due to other influences.
But history will not look kindly on those who dedicate their lives to these dreams of living in space.
Yes, we need dreamers. We need them here. We need them now.