Although content creators, instructors, and students alike see the value in providing interactive courseware to help students learn, they remain a costly solution to create. Platforms that allow the creation and delivery of interactive courseware are only fully utilized by those who can afford the labor cost of building hundreds of formative items just to start. Most of the time this means barriers are too high in either financial cost or extremely long development timelines. Our solution is called SmartStart, a process that works to reduce these barriers to creating courseware by automating basic steps that otherwise require significant manual labor. Automatic question generation (AQG) is one in a series of steps in the SmartStart process that work together to transform textbook content into a courseware learning environment.