The vast majority of people who get such benefits only do so temporarily. And you are right, it is generally a good investment, as you went on to pay much more in taxes than that cheese was worth.
Of course, there are always people who play the system and try to get what they can. But that idea applies to the rich at least as much as the poor, and with more significant results when some rich person takes advantage of the system. After all, when a rich person weasels out of paying as much as middle class people, we are generally talking about a lot of money, not the little bit that some poor person might game from the system. So if we are going to be realistic about what matters most, it is the rich who cheat, not the poor, that makes the most difference. But for some strange reason, many people ignore them and just focus on the poor who game the system.
Who are these so-called rich people who cheat?
The top 1% of income earners, according to the iRS, are people who make something like $400,000 per year in adjusted gross income, and there are something like 1.4 million taxpayers in that class. (Which, I might add, includes married people filing jointly.) What do you think, over 90% of the 1% work for a living? You know, get their income reported on a W2? How do you cheat when your income is reported on a W2? Go ahead, play with a copy of TurboTax and try it. What you'll find is that one of two things will happen. You can try to use deductions and credits to reduce your taxes, in which case AMT will kick in, and you'll see a dollar for dollar increase in your taxes as you add deductions, outside of charitable contributions and mortgage interest. One way or another in 2014 you're probably going to pay at least 35% of AGI in federal taxes alone, and perhaps 39.6%, if you're solidly in the top 1%.
Or are we talking about business owners, who can get creative in accounting for expenses, which I think might be a problem, and what that means is that the number of Americans making over $400K per year is really a lot higher than we think it is, and the top 1% is really at a much higher level than $400K. If that's your point, it's entirely possible, though I'm not sure how to estimate it.
My point is, that people who are paid in wages, which probably make up the large majority of the official 1%, can't cheat much.
What Warren Buffet does, and Barak Obama and a lot of other high-income people do is get a substantial portion of income in the form of dividends, capital gains, tax-exempt interest from municipal bonds, royalties and probably a myriad of other obscure income sources I'm unaware of which are taxed at a rate lower than wages. Should they be taxed at lower rates below, say, $1M in personal income, but at the higher rates for wages above $1M? I'm not sure what I think about that, but such a lariat, indexed for inflation, sure would capture a lot of really rich people paying far less income tax than those who work for wages. And it would exempt the vast majority of people who really do work for a living. Hmmm.