Homelessness is currently at a demographic crossroad. This presents a unique opportunity for hastening its demise. In the thirty years since homelessness first manifested itself in American cities in its contemporary form, it has ascended to one of the most prominent American social problems. Despite the current push by advocacy organizations to end homelessness, many expect it will always be with us. In its longevity, however, lies the potential for its decline, provided we do not repeat this cycle with a new generation of homeless.