I know where you're coming from! Coming of age in the 60s I def thought we'd make a lot more progress by now. Despite Musk I think any planet colonization is very far in the future. I'm not that into planets (for colonization) anyway, I think habitats are the way we'll live in big numbers in space, eventually.
I agree habitats (space born?) will likely be the first step toward humans making any real progress in the (colonization?) of space. Although I also believe that will lead to the eventual colonization of other planets especially if we ever get to one that is capable of sustaining human life.
I also think that commerce will pave the way sort of speak. As supporting evidence of that I offer that without the Musk of the world to look for ways to make a profit out of any space venture. The best we can expect as far as space human exploration will come in is spurts and starts.
Your basic rinse and repeat because your average joe, where the monies to pay for it do and will need to come from; is not interested enough, to keep his attention focused on it, or rather in what's out there ...if there's nothing in it for him.