"thoughts on what puts people into that programming underclass"

An example is the developer that just quoted me on setting up a server. He is charging me essentially his cost for the equipment and 3 hours at $50 per hour to set it up. I've seen this time and time again. Not able to price to what the market will bear. (He's in the midwest by the way and has a stunning resume and full time job working for a known company).

I don't know exactly what you mean by underclass (though I think I've seen a similar comment of yours), but one answer is what plinkplonk said in this thread: immigration restrictions, combined with the concentration of "elite" software companies in the US.