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Some basic philosophical disagreements revolve around this. One mans injustice is another's evolutionary survival of the fittest where patience, planning, and low time preference are strongly rewarded by the system. One mans injustice is lack of equality of opportunity, another's is lack of equality of outcome.

There's a quote often falsely attributed to John Wayne "Life is hard; it’s harder when you’re stupid". Some folks see that as good, some as bad. A classic argument of individualism vs collectivism. Obviously the individual is better off if individual stupidity is not punished and obviously the civilization is better off, especially in the long run, if stupidity is punished, so opinions on punishment usually simplify down to an argument about individualism vs collectivism.

The John Wayne quote is a slightly different thing. I don't think its particularly controversial to suggest that stupidity should not be rewarded as well as the absence of that stupidity (calling it punishment may turn some people off, even if it means the same thing).

The Vimes example is about the fact that being poor to start with is more expensive in its own right.

Vimes does not make a stupid decision not to buy the expensive boots, they are simply more than he can afford in any reasonable period.

There is another saying "making your first million is hard, making your second million is inevitable"

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