As one solution to the problem for condition assessment of existing short and medium span (10-30m) reinforced/prestressed concrete bridges, a new monitoring method using a public bus as part of a public transit system (called "Bus monitoring system") was proposed, along with safety indices, namely, "characteristic deflection", which is relatively free from the influence of dynamic disturbances due to such factors as the roughness of the road surface, and a structural anomaly parameter. In this study, to evaluate the practicality of the newly developed bus monitoring system, it has been field-tested over a period of about four years by using an in-service fixed-route bus operating on a bus route in the city of Ube, Yamaguchi Prefecture, Japan. In here, although there are some useful monitoring methods for short and medium span bridges based on the qualitative or quantitative information, the sensitivity of damage detection was newly discussed for safety assessment based on long term health monitoring data. The verification results thus obtained are also described in this paper, and also evaluates the sensitivity of the "characteristic deflection", which is a bridge (health) condition indicator used by the bus monitoring system, in damage detection. Sensitivity of "characteristic deflection" is verified by introducing artificial damage into a bridge that has ended its service life and is awaiting removal. Furthermore, the sensitivity of "characteristic deflection" is verified by 3D FEM analysis.