I was in this situation. This post plus the grandparent post above it really strike a chord. On one hand, creating a sink or swim environment means I am probably a more resilient person having gone through college with limited family support compared to my peers. On the flip side, I am sure I'd be even more "successful" had I been able to focus more on improving my own skills or grades or academic research than working multiple jobs just to raise cash to pay bills.
The above may sound a little like venting, but it's more to stress the point that financially stringent or irresponsible parents, or parents who just don't believe in investing in kids, is a negative drag on the economy and we are under-utilizing young people's intellectual potential by stressing them out over money.
Related to the top-level post, I'd be angrier at rich families gaming the system except this is absolutely a whole system that needs re-worked from near-scratch.