Lots of people do it. Lots of people always did it. Perhaps at the start of human everything everybody did it - out of necessity.
Last night whilst resting at the end of a long day I watched a BBC documentary all about contemporary nomadic people in the USA. Mid-West USA precisely. Very interesting. It touched on the aspect of freedom, but sort of missed the essential point of the freedom, but introduced itinerant workers, retired travellers, young people effectively running from a society they didn't fit into - much more. Very briefly it touched on the dangers. The lost people. The crazies running from pretty much everything. Understandably, the presenter's focus seemed to be on the enjoyment of a travelling existence whilst trying to point out something he didn't quite point out. I guess he didn't really understand it. That crazy guy you ran from - you have to learn to live with him and many more!
For me, the point it missed most was that increasingly it is not a lifestyle choice. People are having to move to survive. In Europe as much as the US and elsewhere. I love to travel, but the dream I am chasing is a financially secure existence living in the city I love most and doing the work I love most. It is a HUGE ask from life. But, if the choice was there, I wouldn't go the nomadic route.
Travelling costs money. Life costs money. Whilst hobo life is not about paying countless monthly bills it is about paying. Without vast savings in the bank you need income. You can only live for free within very tight parameters. This is not freedom. Recycling from dumpsters at closing hours. Using church run kitchens for hotmeals. Relying on handouts. Spending countless hours on the side of a road waiting for a lift. Being dependent on charity organisations for healthcare. This is NOT freedom. The other route - the 9-5, desk and boss with holidays offers more freedom.
Nomadic life can be free. You need to earn it. You need to know how to survive in lawless societies and strange environments. You have to recognise dangers and deal with them in a very calm, controlled manner. You have to recognise your own weaknesses and know how to control yourself! Most importantly of all; you need empathy on a level you always ran from in your other life of rules and regulation. It is a very complicated world.