Flexible learning approaches to education are important in modern Universities. Students should be able to choose how they will study their courses, and educators should be prepared to support students in their choices, and guide students to employ sound educational methods. This paper considers the experience gained by teaching 500+ students over a period of 5 years using a custom virtual learning environment for teaching Operating System Administration. It highlights some of the common concerns educators may have with flexible study, and demonstrates the statistics around these issues. It also considers the future direction of this style of education to best support the different learning styles of the students involved.