This paper identifies design guidelines for the application of evolutionary techniques to the task of generating practice problems for learners in an Intelligent Tutoring System. To this end, we designed experiments that progressively incorporated an increasing number of the characteristics we expect to find in our target application. These features included noisy evaluations, overspecialization, and the need to mitigate user fatigue resulting from interactive evaluations of practice problems. As we did so, we evaluated the potential of recent breakthroughs in coevolutionary learning theory and identified the tradeoff specific to educational applications.