I am a professional railroad hobo.   I have been hopping freight trains since 1989 and have ridden over 340,000 miles of rails since then as well.  I have ridden all railroad lines that exist in Canada, USA, and Mexico.   My hobo pictures can be seen at:
flickr under the name Hobo "Shoestring".
After I graduated high school and trying the US army for a short time, I hit the rails and have been riding hard ever since.
My OCD was so bad that I could not sit anywhere more than five minutes without getting bored to death, so I found that hopping trains took this upsetting feeling away almost as well as Valium or Librium did!