Look at the reasons many people are 'dirt poor', as Hillary called herself and Bill when they left the White House- lack of schooling, lack of good parenting, generational poverty because nobody in the family bothered to move to find work, dropping out of school and being bad students, drug/alcohol addiction, the feeling that there's no reason to bother trying, mental illness, long-term involvement in gang activity and reaching an age where the gang no longer needs them.....
Then, there are examples of people who gamed the system- we (Milwaukee area) have had many people who demanded that their daughters start having kids at an early age, so they can bring in more benefits. We have had many adults who collected benefits under several names, we have had day care operators filing claims that they had far more kids enrolled than they did and most of the ones who were there were the children of relatives, who also worked at the day care- they were being paid to care for their own kids and those of their close relatives and may have cared for them even if that day care didn't exist. Food stamp fraud, collecting rent assistance when it wasn't theirs to collect, Social Security fraud, Welfare fraud, criminal activity- if these people had put this much effort into their own education, they could have done something constructive in their lives.
Watch the interviews with the families and friends after someone kills or is killed in an inner city- many of them seem to be poorly educated and if it's because their school systems are doing a piss poor job, it needs to change- not only for the people who aren't being educated, but also for the relief of tax payers. Romney made a comment during his run for POTUS about 47% of the population not paying any taxes and it played a large role in costing him the election, but it's true. At the current rate, we'll eventually have more people collecting benefits than paying for them and no society can, or should have to, be in that position.
Many schools stopped their shop classes over the years and where do we find ourselves? With a serious shortage of welders, carpenters and people who can work in several other trades. Granted, the entry-level workers can become a journeyman fairly soon, but how many decide that those jobs aren't for them? These aren't glamor jobs- people don't think of these as little kids as "This is what I want to be when I grow up", possibly because they never saw their parents doing DIY things or having those jobs.
I would bet that many poor people would be able to work in construction, but they may not live where they're needed.
Easy living? Not by a long shot. All someone needs to do is go into the inner city and they'll see just how easy that life is.
It is possible to get out of that cycle, though.
Studies have found that yes, you can break the cycle, but the reality is, let poverty go for 3 generations and it becomes almost genetic.
Civil War reenactment is LARPing for people with no imagination.