The value of improving wind power forecasting accuracy at different electricity market operation timescales was analyzed by simulating the IEEE 118-bus test system as modified to emulate the generation mixes of the Midcontinent, California, and New England independent system operator balancing authority areas. The wind power forecasting improvement methodology and error analysis for the data set were elaborated. Production cost simulation was conducted on the three emulated systems with a total of 480 scenarios, considering the impacts of different generation technologies, wind penetration levels, and wind power forecasting improvement timescales. The static operational flexibility of the three systems was compared through the diversity of generation mix, the percentage of must-run baseload generators, as well as the available ramp rate and the minimum generation levels. The dynamic operational flexibility was evaluated by the real-time upward and downward ramp capacity. Simulation results show that the generation resource mix plays a crucial role in evaluating the value of improved wind power forecasting at different timescales. In addition, the changes in annual operational electricity generation costs were mostly influenced by the dominant resource in the system. Lastly, the impacts of pumped-storage resources, generation ramp rates, and system minimum generation level requirements on the value of improved wind power forecasting were also analyzed.