One of the most depressing moments I've experienced was when I was still in school and we did a charity thing for a month where we'd go to the local homeless shelter and help out with various tasks and interact with the homeless people who would come by the shelter.

The reason it was depressing wasn't what you'd expect, I had expected to feel sorry for them but in turned out that the vast vast majority of them were perfectly happy to be homeless they had no want for a better life, they just wanted handouts and felt entitled to them, it was really a strange experience that stuck with me.