The problem is that financial pressures never improve people. Sure, extreme financial abundance can turn a person into an insufferable, amoral twat; but no one's life has ever been improved by deprivation.
Should a kid spend a summer during high school working a "regular" job so as to understand what bullshit average people have to go through (and to do everything possible not to end up in such circumstances)? Sure. Why not? It's a useful experience, when you're 17, to see what life is like for most people.
On the other hand, Game Theory 101 tells us that forced plays are often lousy moves, and that having more options entails higher expectancy. If your kid, as an adult, has to work crappy jobs that damage his career, while others get to make choices that enable them to have better futures because they aren't worried about month-to-month bullshit, then he's going to end up losing through no fault of his own... and, see, this is commonplace. We aren't actually smarter than the poors (the real poors, not non-billionaire "poors"). We just ended up getting dealt better options, whereas they had to operate constantly under constraint.
If you can take stupid obstacles out of your child's life, you should.
