The American Enterprise has a great short article with graphic showing the huge penalties a working single mother can experience as her income increases. According to the article/graphic, this single mother is better off making $29000 in gross income than $57,000(!) See entire article here.
Note this article is for a woman making use of all available government programs, including housing and childcare.
According to the article, the total value of all the programs for this hypothetical single mom is $45,000! This is more expensive than the Free Money for All proposal. Sorry, we cannot give out that much to everyone and stay solvent. For some people there would need to be benefit cuts — for those people to most effectively work the system. There is not way all the needy are getting the level of benefits shown on the graph. You want to know why there are so many hoops to jump through, look at the numbers.