Tager, I'm TOTALLY there for you, I agree with you.
But I think what some of the others are saying is that if you just threw two random people out there who didn't know a single thing about anything, and you said have at it, one lives on land, the other one lives on water, it is much more inexpensive in all ways (time, energy, money, learning curve, etc ...) to live on land than it is on water. You don't drown on land, your cardboard box in the park doesn't sink destroying the possessions you have, etc, you can just walk from one place to another on land but on the water you need a dinghy.
It is less expensive for YOU to live on the water because over time you have become optimized through your continuous investment of time and energy to be extremely efficient at living on the water, YOU can spend 40$us to install your own rigging, because YOU tager are THE MAN and you ROCK!
But had you taken a different course in life, you could have spent that same time and energy learning how to do roofing, putting up dry wall, and all the rest on a house just as easily (I suspect you probably know how to do that too, but pretend you weren't so gifted and see it from another point of view). Learning to find a free boat, anchoring it, using a dinghy, sustaining yourself, etc, yes it can all be free, but is it easier and less expensive than going to live with your parents ?