A system, method, and computer-usable medium are disclosed for determining a maximum amount to finance based on a plurality of periodic payments. The maximum financed amount of the purchase price of a vehicle is determined based on a plurality of periodic payments, including the cost of vehicle insurance coverage. Data associated with a borrower is retrieved, followed by the borrower providing information related to a target vehicle and a maximum periodic payment amount for the cost of financing the target vehicle and insuring it. Vehicle insurance requirement data, vehicle insurance policy data, and vehicle loan terms data is then provided and processed with the vehicle data and the borrower data to generate a periodic cost for a vehicle insurance policy. Thereafter, the vehicle data, vehicle loan terms data, and borrower data are processed to generate a periodic cost for a loan on the vehicle. In turn, the periodic cost for the vehicle insurance policy, the periodic cost for a loan on the vehicle, and the total periodic payment amount provided by the borrower are processed to generate a maximum amount of the purchase price of the vehicle to finance.