A process and set of tools are proposed to automate the creation of an exhaustive set of flood mitigation scenarios modeled in EPA SWMM5, as well as a strategic planning framework that leverages the exhaustive model scope. Using the proposed method, models are generated for each logical combination of independent flood mitigation alternatives, at each possible phase of implementation (i.e. at every practical phase of investment). Cost estimates and flood risk reduction values are calculated for each flood mitigation alternative and organized into all possible sequences of implementation. The exhaustive set of progressive implementation scenarios is then leveraged as a decision-making tool to provide flexibility in long-term planning: because each phase of investment can be implemented and function independently, large capital improvement programs can be constructed progressively, without having to commit (politically and financially) to the cost of the fully implemented program. With the proposed process and data produced, it is shown that strategic planning can be adaptive and adjusted to favor short-term cost-effectiveness, or optimized within a long-term budget while being able to discontinue investment at any phase in the program.