In an illustrative embodiment, methods and systems for automatically assessing damage vulnerability of a property include accessing digital images of a property parcel having a first structure thereon, classifying features visible in the images, including at least one feature of the first structure and at least one feature present in a neighborhood of the property parcel, to determine at least one of characteristic of each feature, determining a spatial relationship between a first structure and each manmade and/or natural feature represented by the classified features, and applying a property loss risk profile, based at least in part on the determined characteristics and the determined spatial relationships, to calculate a risk estimate for the first structure under at least one risk scenario.