A damage assessment (DA) computing device for determining building damage may be provided. The DA computing device may train a machine learning damage model using historical damage data, identify a plurality of buildings that are susceptible to potential damage from an upcoming weather event, the plurality of buildings including the building, input data associated with a roof of the building to the trained damage model, receive a model output from the trained damage model, the model output including a damage status of the roof representing the predicted extent of damage to the roof, when the predicted extent of damage to the roof exceeds a threshold, automatically generate a claim initiation message including a link that, upon selection thereof, causes initiation an insurance claim for the roof based upon the model output and the parameters associated with the building, and/or transmit the claim initiation message to a user.