Most of the homeless wandering around this town aren't as you describe...the poor, hardworking guy who loses his job, has a lot of medical bills, etc. No, most of the homeless wandering around this  town are drunks who don't want to work. They just want enough money for more booze. Entirely different scenario from what you describe. 
Get real. I know that if I found myself homeless (and I've been close) through some unfortunate set of circumstances, I would be SCRAMBLING to keep myself afloat. I wouldn't have time to sit around panhandling for booze money and then drinking myself into oblivion. Get real.