From a material standpoint, today's homeless people are in better shape than the pioneers were. They get tons of hand-me-down clothes, nobody starves to death, there's no necessary risk for dying from the elements, etc. We have plenty of "urban campers" in the foothills above the U and near the Capitol on Victory Road, but they could be staying in shelters. I've seen some of their camps above the U - really good hardwaret, they have better equipment to deal with the winter than the Martin Handcart company had, without any doubt.
But from a psychological / social esteem standpoint, who would compare today's homeless with the Mormon pioneers who settled Utah? Frankly, we all know the plight of the homeless is pretty bleak. There are a few who prefer that "lifestyle", but most are really, really hurting, it's not a situation anyone would trade places for.
My point is we're finding that "poverty" is really a psycho-social phenomenon, very tough personal circumstances that historically led to early deaths, abandonment, clinging to a tough existence, children going to bed hungry, etc.
So, why all the "despair" the D-News article talks about? Is it Hollywood's fault? Lack of school prayer? We never gave freed slaves "40 acres and a mule"? By any number of objective surveys, many Americans are not very happy people, compared to materially far more impoverished people in many third world nations.
I have some theories, but it's a complicated question that probably defies any single theoretical explanation.