In an illustrative embodiment, methods and systems for automatically categorizing a repair condition of a property characteristic may include obtaining aerial imagery of a geographic region including the property, identifying features of the aerial imagery corresponding to the property characteristic, analyzing the features to determine a property characteristic classification, and analyzing a region of the aerial imagery including the property characteristic to determine a condition classification. The methods and systems may further include determining, using the property characteristic classification and the condition classification, a risk estimate of damage to the property due to one or more disasters and/or a cost estimate of repair or replacement of the property characteristic.