Public transport can be considered both a public good and a private operation. This study focuses on the pricing dilemma that emerges from the need to balance affordability for the public and profitability for operators. Through a systematic review and ex-post evaluation of the pricing policies in Singapore and Hong Kong, we analyze the impacts of various transport policy schemes on the pricing dilemma to draw implications for transport policy making. Pricing policies are evaluated by integrating the theory of change and realist evaluations to observe how fare schemes, subsidy schemes, and finance schemes impact affordability and profitability. The case studies reveal that fare schemes may be less effective in addressing affordability compared with subsidy schemes targeting low-income groups. Finance schemes, on the other hand, set the financial structure of the public transport system and significantly influence the balance of the pricing dilemma and can be reformed to adapt to changing socioeconomic conditions.