A home cost analysis server is configured to train an image processing program to identify features of homes, receive user input including a prospective home, and access a first database storing metadata and images associated with homes, including the prospective home, available for purchase. The server is also configured to input images of the prospective home to the machine-learned image processing program, which outputs a feature of the prospective home, access a second database storing historical ancillary costs, and perform a lookup in the second database to retrieve comparable historical ancillary costs associated homes having a comparable feature to the outputted feature. The server is further configured to analyze the metadata associated with the prospective home, the outputted feature, and the comparable historical ancillary costs to determine ancillary home costs associated with the prospective home, and display the ancillary home costs and an overall monthly cost for the prospective home.