Resettlement undertaken with the objective of reducing disaster risk often narrowly focuses only on reducing hazard exposure. However, when resettlements are analyzed from the perspective of holistic development outcomes, including livelihood conditions, health implications, social cohesion and employment opportunities, they are often found to be lacking. Apart from this contrast between considerations of disaster risk and everyday socio-economic risks at the household or settlement level, resettlement programs also lack a clear focus on achieving wider regional development goals including poverty reduction, economic growth and environmental protection. This relates to the sectorization of attitudes to disaster risk and the lack of integration with development concerns across multiple actors involved. This paper offers an approach: (1) to systematize costs and benefits; and using these (2) to assess policy alternatives that could maximize the beneficial outcomes for the resettlement intervention as well as improve overall sustainability for the urban areas they are set in. This paper first situates “risks” within a larger context of structural risks, and then uses the framework of asset accumulation to recognize the changes experienced by the people as costs or benefits. For this, it goes beyond the resettlement site to a broader regional perspective of the city and reflects on the long-term historical trends as well as future risks created by the intervention in the context of urbanization processes and increasing climate variability. To illustrate the use of this approach in assessing intervention alternatives, the paper analyzes three empirical case studies representing in-situ, voluntary and involuntary resettlements from urban Andhra Pradesh in India.