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.

EDIT: Just remembered this http://www.cnn.com/SPECIALS/cnn.heroes/archive/anne.mahlum.h...

Programs like those would have far more impact than jail.