guy, who looked like a 30 yr old, affable oxford shirt khaki pants type, could've been a college grad working in an office cubicle - guy obviously living out of his car!

Only expressed nod hello couple of time. Saw him having difficult time getting into gym one time. [Dropped anonymous $20 into slightly open window of his car. No idea of what issues are, other than they have persisted over months].

Her job was working with difficult cases of the long-term unemployed, and trying to place them back into the workforce. Their stories were as diverse as the population. She told me about "the professor," an intelligent academic for whom just everything had gone wrong, and he was living either on the street or in homeless shelters. He was one of her success stories, got cleaned up, re-employed, new teeth, ditched the booze, and back on his feet. There were plenty of failures for every success story like that.

I did taxes for "well educated" types for decades. It is shocking to me how many people with very nice incomes are just a few paychecks away from disaster. The housing market crash should have taught people something, yet the construction of half million dollar homes is all over the place. When disaster hits, they aren't ready.

Do smart well educated people not ever learn how to live below their means? Bad things happen to everyone. If your life is set up so that when the bad stuff shows up you lose a roof due to finances, then it's past time to get a better plan. I can see that hot markets like California or New York it might be far more difficult, but outside that? No.

Right now I live in a fairly nice senior living place in metro Cincinnati. Some of the folks here made 4 or 5 times the wages we did and have almost nothing to show for it. The "entitled" mentality is irritating as heck and it's hard to keep my mouth shut sometimes. They need financial help to get the services they need to function at 80 or 90 yrs old. I honestly do not understand why am supposed to feel bad for someone in that situation. Oh I'll help, of course I'll help. And I support a good safety net for people. Stuff happens ... but people also need to do what they can for themselves.

that ended with you being homeless. Sadly, others are not so fortunate.

I am in my late 70's and from poor Appalachia. I've given shelter. I've needed shelter. It is mighty hard to have lived how I have, fairly low income through life, health disasters, long term job losses, farm setbacks, economic downturns... and be asked to feel sorry for someone who could afford expensive homes, cars, private schools, exotic vacations. Closets bigger than my living full of stuff.

I help. If someone needs, then they need. In that moment, the why's aren't important. It isn't that I don't care. It's that I don't understand.

Outside of someone being abused and making a run for it or coming out of a hospital to find their whole family dead and belongs lost to natural disaster in the middle of a major recession.... How exactly is it that someone like me can have just a little bit extra to help, and someone with an advanced degree who spent life earning 10X what I did can't figure out a roof. That I don't understand, and really would like to.

There are many reasons why well paid people end up in dire straits, in my case it was starting my first business. I recovered from that first business, but a lot of people don't recover from setbacks, I would have to know each person personally to get an idea why and that clearly is not possible.

it would boggle the minds of the ones doing the stereotyping.