This project is a proof of concept of what we envision as a broad class of AI-based assistants for course development. It focuses on a tool for building effective course syllabi, which serve a variety of key functions in course development. The syllabus outlines key components of the course and serves as a "contract" between the students and the instructional staff. Course policies must be enforced equitably and worded clearly, particularly in cases where litigation could be involved. This project is an example of a simple tools that can help instructors quickly assess how effective syllabi are at answering student questions by actually simulating asking those questions using Large Language Models (LLMs) and so-called Retrieval Augmented Generation (RAG).