You can count on one hand the number of hoboes who slept in trees, and of those, only one slept upside-down, hanging by his feet. And he was not very nice at all, so you wouldn't want to meet him.
But you're about to. Briefly, so that no one gets hurt.
Wicked Paul Fourteen-Toes was very wicked. He found delight in the infliction of pain, embarrassment and discomfort on his fellow hoboes. He peed in their canteens and flasks. He surreptitiously heated their spoons in the campfire. He filled their bean cans with dirt - or worse - and resealed them (don't ask me how). He would burn a hobo's only photo of a loved one or dog - or accidentally drop them in creosote or a cesspool. He frequently tied his victims' shoelaces together. He once put a weasel and an eastern diamondback rattlesnake into a sleeping bag occupied by Finnish Jim, zipped it all the way shut and proceeded to kick it. He rubbed his gamey arm wound on people every chance he got. He often would convince an unsuspecting hobo that a pretty girl liked him and wanted to meet him, then watch secretly as the hapless man would make a complete fool of himself, getting shot down, laughed at or slapped in the face in front of everyone. He cut the fingertips off of fellow hoboes' gloves, and the toes from their socks. He would also put powerful laxatives in the food bowls of police dogs. He drew the line at bringing physical harm to animals, but he delighted in being chased from a train yard by dogs who were busy laying down a putrid, slippery obstacle for the cops bringing up the rear, as it were.
These are just some of the more harmless things he would do. He also committed more than his share of actual crimes, and it is said - although never proven - that he caused a passenger train derailment near Richmond, Virginia for the purpose of stealing suitcases and "grabbing victims' bosoms" in the chaos that ensued. Sixteen people died in that wreck, and scores of others were injured.
His fourteen toes were not by themselves particularly noteworthy, except for the fact that eleven of them were on one foot. And yes, with that one freakishly-grippy foot, he would grasp a tree branch and hang upside-down from it, and snore loudly and drool deliberately his bacteria-laden spittle upon unsuspecting passersby.
There. It wasn't all romance, choo-choos and sticks-and-bindles in hobo world, was it? Next time, we'll talk about a friendly hobo who did nice things and was liked.