This paper develops a comprehensive analytical framework for evaluating transportation infrastructure investment strategies for asset management considering the impacts of extreme natural hazards and climate change. We integrate quantitative risk analysis (RA) and economic impact analysis (EIA) into a comprehensive assessment of the benefits and costs of infrastructure maintenance, rehabilitation and reconstruction (MR&R) strategies. Moving beyond this, the framework explicitly incorporates the bidirectional feedback/impact between asset management (in normal situations) and risk management (against extreme conditions). To illustrate the application, the framework is applied to a case study on the roadway transportation system of the United States Virgin Islands (USVI), considering flood risk and the impact of future sea level rise. The case study demonstrates quantitative measures of the agency and user cost, risk, and other economic and environmental impacts under different MR&R, coastal flood and sea level rise scenarios. The framework supports high-level decision-making that transportation agencies face such as project prioritization, resilience planning, and capital planning. It can be generalized to analyze different types of infrastructure and natural hazards.