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"