This chapter introduces the approach of holistic evaluation of urban development and investigates local actors and their perspectives on urban development in two secondary cities of the global South. Using qualitative material from case studies in Arequipa and Trujillo in Peru, it is shown, on the empirical level, how stagnating decentralisation processes, resource management under personnel and financial shortages, problems with the institutionalisation of knowledge, policies at the local level that are not oriented toward the long-term, difficult conditions for civil society participation and problems with the social inclusion of new residents challenge the success of urban development in both cities. While in Arequipa, professionalisation and institutionalisation of relevant planning tasks have led to progress in urban development. Trujillo shows that there is high pressure to act in urban development policy, which is not always addressed by the relevant actors, especially due to political grievances. This chapter contributes to a better understanding of the individual development paths of secondary cities and complements the working definition for this type of city by comparing two cases. It draws attention to the perspective of local experts and the projects, resources and actors that are important for them.