In this paper, we address difficulties in ill-structured ship design problems. We focus on issues related to evaluation of commercial system performance, involving perceptions of value, risk and time, to better understand trade-offs at the early design stages. Further, this paper presents a two-stakeholder offshore ship design problem. The Responsive Systems Comparison (RSC) method is applied to the case to untangle complexity, and to address how one can structure the problem of handling future contextual uncertainty to ensure value robustness. Focus is on alignment of business strategies of the two stakeholders with design decisions through exploration and evaluation of the design space. Uncertainties potentially jeopardizing the value propositions are explicitly considered using epoch-era analysis. The case study demonstrates the usefulness of the RSC method for structuring ill-structured design problems.