Urban air mobility (UAM) is a concept envisioning safe, sustainable, affordable, and accessible air transportation for passenger mobility, cargo delivery, and emergency management within or traversing a metropolitan area. While the deployment of UAM will require a network of infrastructure (i.e., vertiports), this emerging concept could face a variety of barriers, such as local opposition, infrastructure costs, and multimodal integration. This paper presents a novel simulation methodology using k-medians clustering and sensitivity analysis to model potential vertiport locations in the San Francisco Bay Area. When controlling for land use characteristics (i.e., parcel size and zoning), the simulation and sensitivity analysis finds that as the number of vertiports increases, the average travel times of trips taken by UAM decrease. The analysis also identifies an inflection point of the number of vertiports at which UAM becomes competitive with driving. The analysis concludes that with respect to size, parcels of 2 acres or smaller are the only locations that allow UAM travel times to be competitive with driving. The paper concludes that neither quantitative nor qualitative factors alone will be sufficient to determine the feasibility of vertiports and overcome community concerns associated with vertiport siting. Metropolitan planning organizations, local governments, and other public agencies will likely need to augment technical analysis with robust stakeholder and community engagement throughout the planning process.