Would not a hobo be protective about their few belongings? Why put it on a stick and carry it over your shoulder, for anyone to grab?

Why not simply walk with it in your hands, like a bag? Don't you still get the same weight/pressure? And you still need one hand to hold the stick, so it doesn't free up your hands either way.

I assume that a backpack is too modern or too expensive to work for a hobo of the kind I envision, who would likely be living somewhere in the late 19th century or early 20th century. (Also, a backpack, while freeing up both hands, is also easy to steal from.)