A system and method that guides a user to record initial and final walkthrough videos, along with audio, of their rental property is disclosed. The embodiments also provide a system that can scan a lease for the rental property, as well as audio from a user's narration of the video, and extract and tag particular features of the video for efficient querying at a later time. The system can interpret portions of the lease that are relevant to particular items or components in the apartment (for example, major appliances) and guide the user to perform a comprehensive inspection of the items mentioned in the lease.