To date, measurement-based WCET analysis and static analysis have largely been seen as being at odds with each other. We argue that instead they should be considered complementary, and that the combination of both represents a promising approach that provides benefits over either individual approach. In this paper we discuss in some detail how we aim to improve on our probabilistic measurement-based technique by adding static cache analysis. Specifically we are planning to make use of recent advances within the functional languages research community. The objective of this paper is not to present finished or almost finished work. Instead we hope to trigger discussion and solicit feedback from the community in order to avoid pitfalls experienced by others and to help focus our research.