Unmanned Aerial Vehicles (UAVs) have become readily available for both the average consumer and professional due to decreases in price and increases in technological capabilities. This work ventured to explore the feasible use of UAV-technology in the area of roof analysis for facilities management purposes and contrast it to traditional techniques of inspection. An underlying goal of this work was two-fold. First, it was to calculate the upfront cost of investing in appropriate UAV equipment and training for a typical staff member to become proficient at doing such maintenance work in the practice of actual roof inspections on a sample set of roofs. Secondly, it was to compare the value of using this UAV method of investigation to traditional practices of inspecting roofs manually by personally viewing and walking roofs. The two methods for inspecting roofs were compared using various metrics, including time, cost, value, safety, and other relevant measurables. In addition to the study goals, this research was able to identify specific benefits and hazards for both methods of inspection through empirical trials. These points illustrate the study as Lessons Learned from the experience, which may be of interest to those Facilities Managers who are considering investing resources in UAV training and equipment for industrial purposes. Overall, this study helps to identify the utility of UAV technology in a well-established professional field in a way that has not been previously conducted in academia.