The American dream is to be a parasite and exploit your fellow man. Everyone yearns to be a landlord or invest a bunch into real estate.

But we will let those we see as our "betters" take advantage of us all day long.

I think it's more that effectively resisting the wealthy taking advantage of you requires a broad, organized political coalition the state is specifically designed to destroy, while "effectively resisting" a homeless guy "taking advantage of your generosity" requires you to just keep walking. People know they are getting screwed by capital and hate it; there's just a much larger barrier to avoiding it.