We young people today (anyone below 35-40, really) are the first generation (and a half?) in quite a while to have a worse outlook than their parents in terms of job availability, job stability, prospects of income, legal protections from abusive employers, and so on and so forth. Unions in the US are nearly dead, and Europe is still moving in the same direction. Fiscal and tax policy in pretty much all Western countries has moved in this direction since the sixties, but it's only recently reached critical mass, since economic growth has started to approach its inevitable ceiling. So: we have lower taxes (albeit with quite a few caveats attached) but the biggest difference by far is for high income groups and those with a lot of capital (not income), and in return we make less money, are forced to lead insecure lives where we're at the mercy of our employers, and have to pay out of pocket for an ever-increasing amount of what ought to be public services. Somehow that doesn't strike me as fair, no.
Ah, yes. All people have the same opportunity and ability to rise above their circumstances, regardless of what those circumstances are. Sure, keep dreaming. That is one of the most glaring logical fallacies of conservative/libertarian ideology. The thing is, poverty creates an environment where good long-term decision-making is a near impossibility, as the stress of short-term survival is so great as to render long-term planning near impossible. There are always exceptions, but that is exactly what they are - exceptions. If you have to struggle to feed yourself and your family, if you're working two or three jobs just to make ends meet - which is the reality for a lot of the working poor in the US - you don't have the luxury of taking a step back to plan ahead. This is what your argument entirely fails to address. The conditions for "mak[ing] good decisions with money and work[ing]" are simply not present, and as such expecting that is entirely unreasonable.
The same goes for people growing up in a society with deeply ingrained trauma, such as Native Americans. You're lambasting them for not making rational choices when they're dealing with living under a system of government that hasn't even apologized for committing genocide against them, stealing their land, and stripping them of their rights for centuries. I'd say that under those conditions, it's quite reasonable to not want to be a "good" or "productive" citizen of that society.
