I'd probably be a street musician and people would pay out of mercy or to just stop as I have no talent in music
Really? Your business plan of having a hobo orgy and charging people to watch seems like a job to me.
Stand at a busy intersection selling those small american flags for a buck, you can buy them from the craft store for about .25cents.
I heard from a hobo league of legends player that you can sustain yourself by selling plasma and living in an abandoned supermarket while playing league at the local McDonald's for free wifi