This thesis is composed of two essays that investigate whole farm planning and crop marketing in western Kentucky. In the first essay, contracting decisions between food corn producers and a mill are analyzed to observe factors affecting the bushel amount farmers contract. Unbalanced panel data containing seven years’ worth of pricing and contract information are used with a fixed-effects model to generate parameter estimates and quantify their effect on bushels contracted. It was found that contract attributes, market condition, and relationship-specific assets had a significant effect on producers’ food corn contracting decisions. The second essay utilizes mixed-integer programming to optimize resource allocation and marketing strategy for a hypothetical farm. Post-optimal analysis is performed to determine non-binding capacities for drying and storage equipment. The model is re-run with these non-binding capacities to observe changes in net returns as well as planting, harvesting, and marketing strategies. New equipment and associated costs are identified, and the change in net returns from the base case is used as net cash flow in a net present value investment analysis. Results of the investment analysis indicate increasing drying and storage capacity is a wise investment given the scenario modeled.