Chapter 1 takes a close look at a unique and state-of-the-art dynamic, structural public housing macroeconomic model (DSPHM), based on an open economy for several key macroeconomic variables, actual and expected, as well as the demand for new HDB flats sold. This Chapter readily adopts the DSPHM for simulating two scenarios, namely a “no change” first scenario and a public housing “deregulation” second scenario. Chapter 2 explores the relationship between several economic factors and the demand for public housing in Singapore and Hong Kong, deploying the innovative and versatile system dynamics model, to shed better understanding on the policy implications of assisted ownership housing. The Chapter assesses the demand for new flats of the Singapore and Hong Kong economies, under certain macroeconomic policy changes, suitable for their unique situations. Chapter 3 is concerned with the underlying structural relationships that affect Singapore’s public housing policy to potentially privatize the HDB concessionary-rate mortgages for HDB homebuyers. Such a potential privatization infuses and sustains price competitiveness among the domestic private banks in Singapore, and lead to improved efficiency among them as well as the Singapore economy at large. Chapter 4 is concerned with the binomial option-pricing model, proposed by Cox, Ross and Rubinstein (1979), which is appropriate to represent the movement of the underlying HDB resale flat prices, subject to private market forces in HDB’s large scale public housing secondary resale market. The HDB Main Upgrading Program (MUP) is a heavily subsidized and highly targeted public housing policy. Since its inception in 1992, the HDB has budgeted some S$3 billion to finance the MUP policy. Chapter 5 recognizes housing affordability to be always an issue of concern to many Singaporean homebuyers because shelter forms one of the basic life necessities. The corresponding private residential market in Singapore offers quality and premium private residential accommodation for homebuyers, who prefer the private residential market. The appropriate affordability model is a multi-factor housing affordability index (HAI) model, which considers the ability to provide down payment and to service the mortgage taken up. Lastly, Chapter 6 offers the book’s conclusion.