The chronically homeless are mostly substance abusers or mentally ill regardless of background. The situation is a result of choices and behavior. You cant fix most of them, just show your fellow man a moment of kindness.
There are people who find themselves temporarily homeless for all kinds of reasons. Many of them are very understandable such as job loss, sudden death of bread winner, sickness.... This is the group of people that can be helped and often are. These people dont want to be homeless and will generally make the choices to remedy that situation.
In the world to come, each of us will be called to account for all the good things G-d put on earth which we refused to enjoy. ~ The Babylonian Talmud
Whenever you get mad as hell about it all, grab your rifle and head outside. If you are the only one there...it's not time yet
"Few men desire liberty; most men wish only for a just master." - Sallust