Systems and methods for roof recommendation based upon cumulative weather damage is disclosed herein. An exemplary computing environment includes one or more processors; and a memory storing executable instructions thereon. When executed by the one or more processors, these instructions may cause the one or more processors to: receive roof data from an electronic device and/or database indicating at least a geolocation of a roof, obtain weather data for the geolocation of the roof indicating the weather over a period of time at least near the geolocation, determine a roof recommendation based upon the roof data and the weather data, and/or generate a roof recommendation signal indicating the roof recommendation.