Do Homeless People Have It Figured Out?

Do you ever sit at a stop signal and see the homeless person with a sign and wonder how they got there? What happened so bad in life that put them on the street, in poverty, open to the elements and begging for their next meal and drink?
I was bored at work the other night and was thinking. I thought how I hate my job, what things I need to get rid of before the move, what things to keep. I was thinking of what bills needed to be paid that week and what ones I was just going to pay early to get them out of the way. In my mind I was budgeting the move, the groceries and entertainment money out of my next paycheck. SO many things going through my head and secretly wishing that I had no care in the world. I thought to myself, "If I were homeless I would not have to worry about any of this." This caused my next thought, "Are we the stupid people working to attain things we want, in turn attaining things we don't want (like bills), when all we really want is simplicity? Do homeless people have it all figured out?"
Ok, run with me on this. Imagine being homeless. You can roam where ever you'd like. People avoid you because they think you are crazy. You get a spiffy cart from somewhere and fill it with all your immediate needs as well as cans and bottles to recycle (see, some homeless are more 'green' then most of us!). You get all the exercise you need to stay fit and all the fresh air to be healthy. You can play in the park all day long and dine on any food you want (as long as you don't mind someone's left overs) depending on what dumpster you want to jump into.
Sure it has its downsides too. It can get cold on the street. Someone else who is more crazy can come up and cut you. You will always wear hand-me-down clothing, and you may not always smell the freshest, but take all that away and WHAT A LIFE!
Is there a way to do both? Live respectably and freely at the same time? Can we have all we really need and be happy with that? Can we suppress our human need to attain things? I think if there were, some of us would have already figured it out and be living that way. I think some already are, but as for me, I could not live like that, but secretly wish I could.