I can personally only vouch for traveling solo as a homeless man. That is the only perspective that I know. But I can’t say that traveling by only myself is a good idea. I have many shortcomings that leave me to be much more vulnerable than a traveling group. For instance, the cops feel like they have an upper hand with harassing me:
What if I was with a group instead? Would this police detective have been as rough with me as he was? He certainly would have wanted to call for backup. If I had other people around, they could have added input and insight into the police harassment. Also, they could be good witnesses as well. Instead, I used my camera. But what good is a camera for the immediate encounter? If I got shot, the camera could have easily disappeared after the cops searched my car upon my death.
Many people travel in groups and have been safer for doing so. It was how the American Indians used to live before the white European set up all these landlocked laws. It’s all a matter of priorities of what suits the people in power at the time. Maybe the Indians were not able to ever secure definite lands because of their extremely crazy and aggressive enemies. Or maybe the lands also make it harsh to live on for very long periods of time.
I slept in my car through a Wisconsin winter and almost a second one. In fact, I never actually was able to completely sleep through the first winter. My moms boyfriend decided to be merciful for January, February, and March and let me sleep in their home. Those are the deadliest months to sleep outside in Wisconsin. I suffered many cold injuries on the other months, but at least the nights tended to stay above zero degrees.
Could a group survive out in the Wisconsin winter better? I have to wonder. They certainly would need to get along with each other well enough, because they would be looking at a lot of close contact with each other to keep warm. Or, they might have a little more money to pool together and leave the frozen tundra for the winter.
With advanced technology in 2014, and ever since Henry Ford made cars cheaper, it certainly has become easier for people to solo the homeless lifestyle. If there is trouble, it’s easy to use the power of the car to get out of questionable situations. But the car is not cheap and cops will still look for it. It’s very hard to hide a car so you can sleep at night. It’s much easier to find a hiding spot when you are on foot or use a bicycle. You can rely on the mass transportation system to get around, although it’s a little slower.
I think I would prefer travelling with a group of other homeless people over traveling by myself. But it would need to be very important to be able to get along with everyone. I would expect a lot of stress to occur during travel and everybody would need to be on friendly terms with each other beforehand. Going into a longterm travel arrangement with people you don’t like will end up in an unsuccessful outcome eventually.