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I'm also homeless living in Winnipeg, MB, Canada right now until the summer comes and we go hitchhiking. I was thinking of making threads like this while we are on the move, but when hitching you never know when you'll have internet, so I've just kept it to my personal notebook.
Staying warm is my only worry, people give generously out here so busking's good.
picture is me in the back, my buddy Matt in the front on last years hitch.