From my perspective, it is about perpetuating the stereotype that rural people are 'slack jawed yokels'. If this guy was from a vertical trailer park (i.e. a high rise condo unit), we wouldn't think twice about it because, despite being potentially just as poor, he is an 'enlightened city dweller'.
I think the people who point out this sort of thing are usually just trying to illustrate that there's all these gossipy judgements we make of each other and that it happens so often and so consistently that we end up doing it it thoughtlessly.
And then there are the people who think the rags to riches tale is just one of the tools of the rich and powerful. That the token success story keeps the rest of us from doing anything to change the status quo. And so rather than being inspired by them they just get grumpy.