This chapter delves into the complexity of sustainable urbanization, climate justice, social inclusion, and participatory governance. Grounded in a one-year descriptive ethnographic study and meta-synthesis, the analysis deconstructs the disparities between the urban rich and poor in Jamaica, Panama, Trinidad and Tobago, and Columbia, across five key development domains- wellbeing, education, security, infrastructure, and governance. Through sociocybernetics, the decision-making processes in urban ecosystems are interrogated, revealing unique challenges faced by the urban poor, trapped in a cycle of recovery, versus the mitigation-oriented urban rich. The analysis extends to the role of urban citizens, designers and integrators, governance structures, levels of social inclusion, resource allocation, and their amalgamated implications for socio-climate justice. It evaluates the international policy arena, translation of global mandates into local development plans, and the need for hyperlocal strategies that encourage a more people-centred planning approach for sustainable urbanization.