TLDR: i'd take unhappy-rich over hungry-poor any day. But the best thing would be the happy medium where you are comfortable enough to afford food/schooling but not in a social class where there are obscene social expectations to spend -- so your question is a fair one.
I think the key thing was getting past the lower rungs of the Maslow hierarchy. It is very difficult to concentrate on schooling (or anything) when you are hungry or sick. I was constantly hungry when we didnt have free public school meals. A close relative had TB, due to poor healthcare where the hospital/system didn't seem to give a darn. The worst thing is how horrible normal people treated you (even teachers at public school.) I was constantly sick, probably due to poor nutrition.
College was great, I will still poor, but the prospects were getting better and all the basics were covered (no longer hungry; decent healthcare). This allowed more happiness because you knew it would be over soon.
With better jobs comes more stress -- the expectations (perhaps justified) that one should have a home, that one should have a school for children w/o crime/gangs -- and bigger mortgages, bigger spending. I live fairly conservatively despite decent career success, but I can see how I could "become unhappy trying to reach happiness"
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all that said, i'd take unhappy-rich to hungry-poor any day.