Bring a pet
No one loves you. Everyone but you knows that. You need to use every resource at your disposal to make people feel sorry for your hobo lifestyle so why not play the pitty card. Bring a pet along for the dirty ride.
People love pets but they extra hate the hobos that have them so it’s a gamble but if you think of you and the furry critter as a hobo unit you get bonus pity points. (Editor’s note: You actually lose points if your name is Critter).
Best case scenario, you get extra change to feed you and a dog. Worst case, you only get a can of dog food. Either way, you’re getting a can of dog food for dinner.
If it fails you can eat the pet.