The idea of a "hobo" has always had a slightly humorous & nostalgic quality that has even sprung up on The Internets.
The documentary, however, was pretty sobering look at the crushing poverty faced by people in the early part of the 20th century. There were no social safety nets nor business opportunities of any kind. Even after all these years, the memories of loneliness & hardship were making some of these old dudes break down sobbing during their interview.
This tragic era is a historical reminder for those who think that Capitalism is the answer to everything. Interestingly, at the end of the program, there was also a look at President Franklin Roosevelt's remedy for the conditions causing the hobo phenomenon.
The government implemented the CCC, or Civilian Conservation Corps. This was a New Deal program that put millions of young men to work creating national parks & other projects. This is exactly the kind of investment that should be made right now to create jobs & improve the country. Of course, free market conservatives would go ballistic over any such thing being created nowadays. I'm sure Fox News would endlessly run headlines about "Obama's Socialist Work Camps" if such a visionary program were implemented under this President.
Incidentally, I've also previously watched the excellent American Experience episode that focuses specifically on the CCC: