I'll toss in the counterpoint that having kids that are thrilled to see you, even if you live in a tiny apartment, is anything but mediocre.
The OP seems to have a lot of priorities out of whack.
When you come from the country club life (first paragraph) it is indeed mediocre.
I would consider that mediocre as well, and I grew up about as far from "country club" life as you can get. As in, dirt-poor, below-the-poverty-line, white-trash from rural southeastern NC.
Of course, some of that is that we constantly raise the bar for ourselves (well, I do anyway). Maybe the scenario above would have sounded like heaven to me when I was 20, but it doesn't now. Just the "job" part gives me the creeps. I, for one, don't want a traditional "job" at all. My standard of the line between mediocre life and successful life involves a big element of being able to control my own fate to a greater degree, and some ability to call my own shots. Translated, that means running a company I own, not working for somebody else.
The OP seems to have a lot of priorities out of whack.
Meh. Who are we to judge? A person's priorities are their priorities... there is no "right" or "wrong" on this.
Absolutely. But, personally, I would find that preferable. There's a big difference from having to be accountable and responsive to "the market" in the aggregate (and especially when you consider that you can "fire" a bad customer) and having a "boss" - one individual who has you under his/her thumb and can unilaterally order you around.
Hands up everyone who had their priorities in life sorted by the of 23? (Mine is down).
So when I go home and visit my friends, and watch them playing with their kids and kissing their wives, etc., there's always a pang of regret that says "you could have gone this route instead". But, of course, as they say "the grass is always greener on the other side of the fence", blah, blah.
But I never wanted to start a family until I was in a position to give them the kind of life that I would want them to have.
Anyway, getting married and doing all that is potentially still in the cards. Time will tell, I suppose.