Methods and systems for automating insertion of content into media-based projects are disclosed. In one embodiment, images are uploaded from a user device to a server. The server performs image analysis on the uploaded images and obtains automatic image information. After presentation of the initial project, the user manually interacts with the uploaded images to provide user inputs to the project. The system observes the user interactions to generate manual image information based on the user interactions with the project. Based on the automatic image information and the manual image information, the present invention automatically updates a printable photobook or other media-based project after automatically inserting relevant content into the project. This produces a faster and more seamless user experience, and increases the number of customers purchasing the ultimate product by minimizing friction points to purchase.