Apologies in advance, this will be part reply to your comment, part reply to the Cracked articles, and part rambling:
Seconded. I was very poor twice in my life. First while growing up, and then for a few years after the downturn (19-23 years old) where I was making 13K-17K per year (post tax/credits, benefits included), working full time, and putting myself through school. I had no financial aid due to having no contact with my parents (a corner case that is poorly handled by the government, try getting anything except loans without a FAFSA). Until two and a half years ago I probably spent only three or four years where I wasn't poor by any standard.
Poverty is definitely something you need to live through to really understand. You can have compassion, commiserate, etc but not a true comprehension unless you've been there. Even then, I know there are levels of poverty I have no understanding of. One I personally experienced was trying to get some help at a free clinic and being denied because I wasn't quite poor enough to qualify. I believe I needed to have a dependent of some kind at my income level. Living through that is something I can't fathom.
Moving is definitely an interesting game. Most of the time I was poor as an adult I lived in a retail store front (that couldn't be rented out, leaky roof, boarded up windows) for $300/month. When I started doing well enough (making more than 20K) to consider an apartment, I went in with three friends because the cost to just get into a place in LA is typically, at minimum, $2000. The lower rent apartments want first, last and deposit, while more expensive apartments just want first and deposit. It's basically impossible to save up 1/10th of your gross yearly income, and it's not like the money is guaranteed to come back to you.
Since you're in a bad spot, and the landlord knows it - otherwise you wouldn't be one of three people in a $1400/month two bedroom apartment, they will play games with you. We had broken plumbing that went unfixed. None of us saw our deposits back. The management company literally pulled down websites as I found phone numbers for people in their offices. For a brief, albeit melodramatic, moment I felt like the protagonist in a man v.s. the oppressive company/government/world movie where I had just caught them and they were trying to pull the curtains over their wrongdoing.
Since I was still working insane hours and going to school, the couple hundred dollars weren't something I could chase after... which is really the sad thing. They knew I couldn't afford to do anything about it. Being inexperienced doesn't help. Yes I could have gone to the city, but I didn't know that back then, and when everyone around you is in the same place, you're often times short on experience. (I've since launched complaints after the fact - I'm not the first this has happened to ;). It's in the city's hands at this point)
Now that I'm doing a lot better, the Cracked articles really hit home. My personal poor habits from those articles is limiting myself to two/three pairs of pants and the paranoid bank account check habit. Even though I typically keep my expenses at half or less of my wages and I know the money is there, I won't sleep that night if I don't check my accounts every few days. When I was poor the next disaster seemed to be right around the corner. It's really hard to shake that instinct.
Being able to really live has been very interesting. I've tried to do as much traveling as I can, something I could never do before. I find myself weighing every permutation of airfare (travel dates, airlines, buying separate round trips for multi city trips), just like I used to do once upon a time when figuring out how to buy a month's worth of groceries in $60.
That said, I'm not immune to doing bad emotional math. I just got a bonus today and the same thought process ran though my head when I saw the amount deposited into my account. It's hard not to. In fact, musing about it is enjoyable. Much more than being rational about it. Money brings out all sorts of emotions.
The problem I have with it is that I like roads, police officers, and all those expensive "leach-feeding" social programs I used to be a customer of; so I quell my irrational anger pretty quickly. Without inexpensive Community College courses I wouldn't have gotten the necessary education or the connection I used to get my first paid internship ($15/hour almost double my previous job) which turned into my career.
Like the Cracked author mentions, yes there are terribly abuses of the money... but I believe the good outweighs the bad.
I don't see any problem with paying that forward. I'm certainly not suffering doing it, even if I occasionally shake my fist at those "Tax and Spend Commies in Congress" for an irrational split second. In a couple years, with some luck and hard work, I'll be making closer to the amount that poor unhappy retired couple from the WSJ graphic was making[1]... all the while dealing with my "poor kid from North Hollywood" mentality.
[1]http://online.wsj.com/article/SB1000142412788732368960457822...