The other fact that you barely touched, is that the well educated who come to discuss this stuff on /. have a good overview of the whole situation. We were discussing these things as if we were suddenly body swapped with underprivileged teenagers, in which case, of course we would know optimal course to maneuver ourselves back into the middle class.
They guy you spoke of probably had no concept of the tiny slice of a career map that would be available to him. The unemployed that I've met, often don't even know how to start a coherent job search.
We middle-classers also think it's easy to find the optimal apartments and part time jobs given that we have reliable access phones, vehicles, nice clothes and the optimal sources to get the latest listings. When you don't have these things, it's nearly impossible to find even that low paying job. And if you think you might lose it, are you really going to invest your first few months salary in an apartment (plus security deposit and whatever fees the landlord charges you for not knowing your rental rights) and vehicle?
Plus, each of those needs is itself, a struggle to get without the unappreciated gifts of being middle class. You mentioned HUD, but a little known fact about renting, is that though owners legally have to accept HUD, if you mention it, they just stop returning your calls (assuming your alcoholic parents will take a coherent message for you, and don't scare the agent). I also learned, that at the last two places I rented, I beat out the other guys just by being a sharply dressed white guy* with sober contacts. Oh yeah, forgot to mention, you need three of your buddies to own phones, speak well formed English sentences and answer with polite sobriety for the entirety of your house and job search.
As for the vehicle (this is the US we are talking about, good luck without a vehicle). Some people are usually willing to part with their vehicles to anyone with money (which you have to find first, maybe once you've got that job you can sell your soul to payday loans), but I've had a friend ticketed for improperly disposing of a vehicle years after the sale; turned out the buyer decided to negate the transfer of ownership (illegally). To avoid these problems, many people also screen who they sell their cars to. I myself don't drive around to find you so you can test drive my car, so you also need to find a reliable friend with a car just to buy used (gas guzzling, mechanically unlucky) cars from rich folks like me (sorry).
*Like HUD, owners can't be caught screening against single women or minorities, but they do anyway.