Perhaps this is true in some strictly literal sense, but we could argue all day about whether the responsibility for that judgement and those choices really lies with the homeless person in question, or with our culture, education, and society.
If a lot of apparently sane people make (disastrously) bad choices, I think it should be our first inclination to consider where the bad choices are coming from, and perhaps try to help them make better ones, before we dismiss the issue as some individual flaw.
Let's be realistic here: you don't know what you're talking about at best.
Those who are homeless tend to be so for a few reasons:
* Being a battered wife who has finally decided to leave her husband;
* Being mentally ill without the support structure to ensure that you have all of the (expensive!) medications you require and/or treatments that keep you stable enough to be productive to society;
* Losing one's home to a fire or other disaster without sufficient insurance to recover from it (if one could even afford or qualify for insurance) or where the insurance company refused to pay for legitimate damages (see also Katrina);
* ...and exercising bad judgement and choices over time.
Any of those you said, can happen to anyone, anytime. If a family is living paycheck to paycheck, something like this happens, they can be financially ruined and become homeless in just a few months.
Yes, they might have been irresponsible, might have made bad choices. But many people end up homeless, for reasons outside their control (bankruptcy, families abandoning them etc). In any case, their 'crimes' are nothing compared to those like Madoff.
These homeless people need help, not punishment and fines.
Let's be realistic here. One generally ends up in that situation by exercising bad judgment and choices over time.