Structural health monitoring is effective if it allows us to identify the condition state of a structure with an appropriate level of confidence. The estimation of the uncertainty of the condition state is relatively straightforward a posteriori, i.e., when monitoring data are available. However, monitoring observations are not available when designing a monitoring system; therefore, the expected uncertainty must be estimated beforehand. This paper proposes a framework to evaluate the effectiveness of a monitoring system accounting for temperature compensation. This method is applied to the design process of a structural health monitoring system for civil infrastructure. In particular, the focus is on the condition-state parameters representing the structural long-term response trend, e.g., due to creep and shrinkage effects, and the tension losses in prestressed concrete bridges. The result is a simple-to-use equation that estimates the expected uncertainty of a long-term response trend of temperature-compensated response measurements in the design phase. The equation shows that the condition-state uncertainty is affected by the measurement and model uncertainties, the start date and duration of the monitoring activity, and the sampling frequency. We validated our approach on a real-life case study: the Colle Isarco viaduct. We verified whether the pre-posterior estimation of expected uncertainty, performed with the experimented approach, is consistent with the real uncertainty estimated a posteriori based on the monitoring data.