Fence Straddlers and Land Owners

We all know what a fence straddler is and the only real analogy I could come up with in opposition was a land owner. People that actually commit to buying property, building a home, nurturing their land, and growing something really valuable. Maybe even taking on a few animals and growing a garden.
Fence straddlers hem and haw and try to convince land owners that they are way too up tight and take things way too seriously. Land owners prevent fence straddlers from living life and whoopin' it up. Land owners spend too much time planning for the future and earning their life.

Yet, in the winter when the fence is cold and there are no walls surrounding the fence, and the wind is blowing, the fence straddlers want to come inside...where it's warm and dry... and there's food. Fence straddlers wonder why they never have enough.
Land owners don't have it easy but they are comfortable.
Fence straddlers don't have to commit to anything.
Land owners must commit to everything - growth in fact takes commitment.
Land owners probably are boring and dependable.
Fence straddlers represent youth and fun times. Who wouldn't want to be a fence straddler?
Can someone tell me the long term benefits of being a fence straddler?
I mean I'd love to try it, but it's hard to become a fence straddler once you've been a land owner. I mean expectations of lifestyle come into question and then there are the people who depend on the farm. But, if I was to want to become a fence straddler - explain to me what the gain would be - personal and long term.