Diagnostic instrumentation and monitoring of bridges are essential for reliable structural condition assessment and performance evaluation. This management step applies particularly to structurally deficient bridges that cannot be accurately evaluated by inspection and/or analysis alone. Reliable evaluation is an economic and engineering requirement before any decision-making for preventive action. Thus, field diagnostic capabilities are indispensable tools to enable evaluation and support field-calibrated modeling, analysis, identification, and load rating. The reliability of structural evaluation for objective bridge management is determined by the dependable performance of all the system components. Although instrumentation and monitoring procedures appear to be well established, some misconceptions still keep recurring critically in practice. To improve the state-of-practice of structural diagnostics, available field systems and methods need re-evaluation of their instrumentation and monitoring performance under real-world conditions. Subsequently, dedicated field capabilities can be formulated and developed to have advanced and practical characteristics. This article discusses various less-emphasized critical aspects of multidisciplinary research experience on bridge structural health monitoring, to explore dependable evaluation methods, compile practical data on actual bridge monitoring for immediate implementation, and generate focused insight for the development of advanced, reliable, and practical research methods in the future. To reach a systematic conceptualization for a better methodology, various diagnostic components are criticized. The resulting discussions on the various bridge evaluation aspects are practical for transportation agencies, bridge officials, and researchers. The detailed aspects are intended to help select appropriate implementation practices in field applications of bridge instrumentation and monitoring. These help focus bridge management policies, re-orient evaluation strategies, and reconsider diagnostic methods.