1. A computing system for generating a roof report, the computing system comprising: a memory; and a roof estimation module that includes a calibration module, the roof estimation module being stored on the memory and being configured, when executed, to: receive a plurality of aerial images of a building having a roof, the plurality of aerial images having been taken independent of each other, at different times and on different dates, the aerial images providing different views from each other of the roof of the building, the plurality of aerial images including at least a first aerial image that is a top plan view of the roof and a second aerial image that is an oblique perspective view of the roof wherein at least one of the first and/or second aerial images is calibrated using calibration information received from the calibration module; perform image analysis on at least two of the plurality of aerial images; calculate a pitch for each one of a plurality of roof sections of the roof based on the image analysis; generate a roof report that includes the pitch of each of the plurality of roof sections based on the calculated pitch; and output the roof report, wherein the roof report includes one or more top plan views of a model of the roof annotated with numerical values that indicate a corresponding pitch, area, and length of edges of at least some of the plurality of roof sections using at least two different indicia for different types of roof properties.