I'd think more in terms of transits and progressions to the natal chart as one isn't homeless all one's life.
Neptune, the planet of Divine Discontent. Nothing of this world ever satisfies Neptune. Only inner work will get Neptune to quit being so ornery about worldiness.
BTW...if you know of anyone who is homeless, and needs help, I'd recommend Neale Walsch.
As you may know, he went from homeowner, to totally messed up homelessness, then wrote a book that became a best seller.