1. A method in a system for generating estimated wall area measurements including a computer processor and a memory coupled to the computer processor, the method comprising: receiving roof measurements of a building having a roof; receiving a measurement indicative of a distance between at least one reference point on the roof and a ground surface on which the building rests via a placement of a graphical user interface element representing a horizontal planar model ground surface at a position beneath a graphical user interface element representing a digital three-dimensional model of the roof; and generating, based at least in part on the received roof measurements and the received measurement indicative of the distance between the at least one reference point on the roof and the ground surface, an estimated wall area measurement of the building.