The evolution of Affordable Housing initiatives around the World suggests that while in the early stages the government plays the role of the developer supplying affordable housing units to a growing population, a transition from the Supply side to the demand side, providing financing solutions and products as well as becoming the regulator of housing activities, must happen expeditiously to avoid imposing dead weight on the private sector. Different countries around the world have had different success rates. While some were successful in evolving from a supplier of affordable housing to a regulator of housing initiatives, others have failed to do so with drastic consequences. This paper demonstrates the various journeys undertaken by various countries in the Affordable Housing Initiatives.