Make no mistake, it is a horrific life choice. People gamble away their life savings, their children's college fund. It ruins marriages and families and can utterly wreck human beings. But if we are to have freedom, you have to have freedom to choose. Otherwise, you really don't have freedom, you have people living their lives according to proscribed rules.
For example, in a recent Reuters piece, an author examines the idea that some folks believe that debt will outlast their lives. According to a survey by Northwestern Mutual Life, 14% of Americans believe that debt is a life-long condition. They profile one lady who is my age (57) and has $20,000 of student loan debt she cannot seem to pay off. She joked the loan would still be there when she died.
So while it puzzles me that a guy would live in a trailer home surrounded by crap in his yard, this does represent "freedom" in this country - freedom to make what I perceive to be a bad choice in life (he no doubt thinks otherwise!). We could force people to make different choices, but it likely would be nearly impossible to enforce, and moreover, would negate the concept of freedom - freedom to fail, freedom to make crappy choices, freedom to be stupid, in fact.
What I think browns-off a lot of people is that the same people who say they want freedom to make bad choices often are the same ones who decry the welfare state and yet, when their bad choices catch up with them, are the first in line to collect government assistance. You see the irony here. But then again, being poor and voting for Donald Trump is part of that freedom package.
So I guess this is why I am not one of those on the left who wrings their hands and "feels sorry" for "those less fortunate than ourselves". They have the freedom to choose, and if we subsidize bad choices, not only are we making a foolish move (by encouraging bad choices) we are, in a way, negating freedom.
You can't have freedom to win, unless you have freedom to lose.