As the National Association of Broadcasters moves into a more operationally focused phase of developing Broadcast Positioning System (BPS) infrastructure, long-term performance monitoring and analysis has emerged as a significant need. This paper describes the design of a system for measuring and visualizing BPS performance using time-series data and stability metrics such as MDEV and TDEV. It also outlines the iterative, AI-assisted development process that enabled the monitoring tools to evolve rapidly in response to stakeholder feedback, resulting in a robust framework for assessing accuracy, diagnosing anomalies, and improving the reliability of broadcast positioning and timing systems.