To dream of a homeless person represents an aspect of your personality that has experienced total failure. An area of your life that you have totally lost control of or that's completely powerless.
Alternatively, being homeless in a dream may reflect anxiety about financial hardship or low confidence in your future.
Example: A man dreamed of being surrounded by homeless people. In waking life he had just lost a competition at his work place and lost out on a opportunity to be promoted.
Example 2: A young woman dreamed seeing a homeless man with his hands out begging. In waking life she was dumped by her boyfriend and would have done anything to have him back.
Example 3: A woman dreamed of being homeless. In waking life she was pregnant and having anxiety about going broke supporting the baby.