A system and method for evaluating the risk of insuring a grower comprises a communications interface for obtaining a geographic area yield (e.g., mean geographic area yield) of a crop for a particular geographic area (e.g., county) for a corresponding time period. A yield monitor or a yield sensor, associated with a ground-based or aerial work vehicle, obtains a benchmark grower yield (e.g., historic grower yield) for a particular grower within the particular geographic area. An analyzer determines a difference between the geographic area yield and the benchmark grower yield (e.g., historic grower yield). An estimator estimates a variability parameter indicative of a variation in forecasted grower yield in the geographic area. A data processor determines a forecasted grower yield, which may deviate from at least one of the geographic area yield (e.g., mean geographic area yield) and the benchmark grower yield, for the corresponding time period based on the difference and the variability parameter. A data processor determines a risk indicator based on the determined forecasted grower yield.