While I know you inteded this as a direct question, I'm actually going to give a meta-response. It seems to me that you think that the problem I'm outlining in my "train" analogy is that I personally am not on the train. To the contrary, the problem is that there is a train at all. Even if/when I manage to climb safely aboard, I'll have left behind an entire class of people who weren't so lucky. Smart, capable people who just wanted to do something respectable and beneficial for the world, like teaching or journalism or home health aide. I understand that all those people could just give up on what they're doing and "learn 2 code" but I think it should be obvious that (a) not everyone wants to code (or can do it to a high level), and (2) a society made up entirely of coders is not desirable.
More broadly though, I suspect you and I just have totally different worldviews. You correctly point out that there are straightforward steps to escape the crushing hopelessness of life in the modern underclass. What I'm saying is that it should be made possible and in fact easy for people to carry on a dignified, non-hopeless existence without being coerced into chasing the absolute highest-paying job available. I suspect this comes down to personality. If you're satisfied living "defensively," putting aside what you most crave or are actually best at in favor of the thing that will keep you protected while the rest of society atrophies, well that's lucky for you. But not everyone is wired that way. If we were, I doubt things like good food or art or music would exist.
As for the dating thing, if you're not on the dating market right now you might not be aware that COVID massively messed things up. People now (myself included) are weirder than pre-2020. Human connection is harder. In fact, I'm going on IRL dates from apps most weekends now, but it's still a struggle compared to how things used to be, for me at least.
I doubt anyone is still reading by this point but I will say this: my original post was not about how my life is falling apart. I suspect I'll be fine; I'm doing more or less exactly what I want to do, all day, every day. The issue is, net net, lots of people are struggling. If people pulling themselves up by their bootstraps was a viable solution, we'd live in a utopia by now.