Maybe that's because you're homeless and don't want to be. The Leatherman could have settled down, per the article he "had money", but he just didn't want to.

I was intentionally homeless for 4 months, just riding my bike all around western Europe, just setting up my tent in a random woodland every night. I didn't have a safe harbor, except for the knowledge that I could get a job and rent an apartment if I wanted to.

It was not hard at all. In fact, I loved every minute of it. I lived/worked on a farm and slept on a bed for 2 weeks(WWOOFing), and I could not wait to get back out on the road again.

Camping with money for 4 months is not homelessness! Thats such absurd idea.