One of the few decent spots in my town is a concrete foundation that is adjacent to a rail yard. A couple of years ago I was skating there and saw some dude sitting in the bushes, he was watching us skate. My friends were creeped out, but I went to talk to him. His name was Chuck. Him and another dude(Roger) lived on an abandoned train car.
I don't know why, but I've always been intrigued by homeless people. Anyways, I ended up befriending these dudes. I would bring them my old clothes, blankets and even started buying them groceries when I would do my shopping. It ended up being a mutually beneficial arrangement. They chased away some kids that were messing with the obstacles we had set-up at the spot.
I had to put a stop to my charity, Chuck started taking advantage of my goodwill. He began to ask me for stuff...smokes, booze, rides to the liquor store...