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ABSTRACT: This study aims to first investigate if the market-force hypothesis and upgrading hypothesis still hold in explaining the demand for first-hand housing development board (HDB) flats in Singapore. Then, simulations are carried out via system dynamics models to assess how policy changes, differentiated in scales and frequencies, affect such demand. The findings, while refuting the market-force hypothesis, extend the upgrading hypothesis, as capital appreciations through selling in the resale HDB market not only contribute to the upgrading of properties among HDB owners, but also provide incentives for nonhomeowners to make the first move in realizing the “Singapore Dream.” Further, simulations point out that either too few or too many institutional changes in response to market adjustments render the HDB system unhealthy. The former induces fluctuating demand, while the latter likely generates extra administrative cost that could cause long-term effects on the financial position of the HDB.