This study investigates the broader challenge of conducting vulnerability assessments in transportation planning, particularly in rural regions where balancing federal funding mandates with local infrastructure priorities presents significant complexities. Vulnerability assessments are essential tools for identifying infrastructure risks, yet their effectiveness is often constrained by funding eligibility requirements and policy frameworks that may overlook locally significant assets. This research examines how vulnerability assessments can better integrate data-driven methodologies with community-informed insights to ensure equitable resilience outcomes. Drawing from established frameworks like those employed by the Genesee and Ulster Transportation Councils, this study explores strategies for improving vulnerability assessments in the Watertown Jefferson County Transportation Council (WJCTC) region. The study highlights the need for improved flexible funding models, enhanced local engagement, and tailored assessment frameworks to ensure that critical infrastructure in Watertown is effectively identified and prioritized, particularly for roads and facilities that serve underserved communities or face heightened climate risks.