Today, Manufacturing companies are adopting a servitization strategy and Product-Service System model to enhance value and remain competitive. Often, this transition also means to embrace a System-of-Systems (SoS) perspective. Concurrently, companies face challenges with volatile, uncertain, complex, and ambiguous (VUCA) environments. One way to tackle VUCA is to utilize simulation modeling. However, developing SoS simulations can be complex and cumbersome. This paper extracts lessons learned from six case studies to identify effective and ineffective practices in developing simulation models. The analysis has led to nine design principles for more effective simulation modeling. Furthermore, the paper explores simulation techniques for modeling SoS and discusses effective VUCA management. Finally, the paper proposes four future research directions to advance SoS simulation research.