Larger acreage farms and even moderate sized farms employing custom applicators and harvesters often have multiple machinery in the same field at the same time conducting the same field operation. For nearly all these multiple-vehicle operations, over application is a concern especially for irregularly shaped fields however modern technology including automated guidance and automatic section control allow reduced doubling of input application including seeds and spray. However, this technology relies upon coverage maps to be continually updated and shared between the machinery; and utilizing cellular connectivity in rural areas known to have reduced service levels. We evaluate the benefit of using multiple planters and sprayers in the same field at the same time, and estimate the cost of experiencing cellular connectivity outages over a range of expected uptimes. We report on the willingness-to-pay for guaranteed connectivity uptime by farmers.