Hobos - as in the ones that actually rode feight, would not have in any way been carrying a bag on a stick - at least while traveling on trains. You NEED both hands, and especially back then. We are talking about a time when folks were still "riding the rods". You wouldn't have had much with you, and you would need it tied close to your body or you could get killed.
There are lots of old photos of hobos, maybe 1% show a pack of this type, on a stick.