My project utilizes OpenAI's image recognition technology to assess the housing conditions and potential for property conversions into duplexes or triplexes in Cincinnati. This is particularly relevant given the city's swift transformation and recent zoning relaxations that promote densification along Bus Rapid Transit (BRT) routes and neighbourhood business districts. Instead of developing a new application, I use existing OpenAI data to analyse images of properties to determine their structural suitability and compliance with local codes. The focus of the project is on the East Price Hill neighbourhood, specifically around Whitter Garden Park. This approach allows me to provide local development advocates with essential data on property conditions, aiding in the strategic enhancement of community infrastructure. By leveraging AI in urban planning, this project contributes valuable insights into housing conditions and densification potentials, serving the needs of Community Development Corporations and housing advocates.