The Highway Safety Manual (HSM) estimates roadway safety performance based on predictive models that were calibrated using national data. Calibration factors are then used to adjust these predictive models to local conditions for local applications. The HSM recommends that local calibration factors be estimated using 30 to 50 randomly selected sites that experienced at least a total of 100 crashes per year. It also recommends that the factors be updated every two to three years, preferably on an annual basis. However, these recommendations are primarily based on expert opinions rather than data-driven research findings. Furthermore, most agencies do not have data for many of the input variables recommended in the HSM. This dissertation is aimed at determining the best way to meet three major data needs affecting the estimation of calibration factors: (1) the required minimum sample sizes for different roadway facilities, (2) the required frequency for calibration factor updates, and (3) the influential variables affecting calibration factors. In this dissertation, statewide segment and intersection data were first collected for most of the HSM recommended calibration variables using a Google Maps application. In addition, eight years (2005-2012) of traffic and crash data were retrieved from existing databases from the Florida Department of Transportation. With these data, the effect of sample size criterion on calibration factor estimates was first studied using a sensitivity analysis. The results showed that the minimum sample sizes not only vary across different roadway facilities, but they are also significantly higher than those recommended in the HSM. In addition, results from paired sample t-tests showed that calibration factors in Florida need to be updated annually. To identify influential variables affecting the calibration factors for roadway segments, the variables were prioritized by combining the results from three different methods: negative binomial regression, random forests, and boosted regression trees. Only a few variables were found to explain most of the variation in the crash data. Traffic volume was consistently found to be the most influential. In addition, roadside object density, major and minor commercial driveway densities, and minor residential driveway density were also identified as influential variables.