Personal property inventory systems and methods include a computing device that analyzes images of rooms in a residence to identify personal property items. Identified personal property items are compared to a predetermined schedule of items that is based in part on purchase transaction data for at least one resident. If an item on the schedule is not one of the identified personal property items, an inquiry to a user in the residence is made to clarify whether or not the item is in the room. Based on the analyzed images and the received answers, a personal property inventory is generated.