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This particular dude is a middle aged white Trump supporter with mixed race kids that were taken away from him.

With transients you're not even talking about the 'working class' or lumpen proles in most cases. In terms of class position this is the lowest of the low - though the working class should be rejected anyway. Work should be rejected in principle. As such I'd say it is heavily dependent on race. Whites for Trump. Non-whites against. At least in my general area. I did meet one Hispanic homeless dude that said Trump finally said something cool and that he might vote for him though.

Of course some are just politically apathetic. Like everyone else.

But yeah, you can vote as a homeless guy. You can get mail. Establish residence at charities, churches, etc. You can do most things to plug into the system. Even get an Obama phone. If you want to that is.