For engineered systems, one of the first decisions a designer must make is the architecture that will solve the established high level function. In most cases, this can be accomplished in a multitude of ways, with each original architecture having strengths and weaknesses. This paper explores how the architecture choice for a system impacts the ability to evolve and meet future needs. The lessons learned from this paper are extracted from a case study where three systems that perform the same task via different architectural solutions are considered. These systems are them compared to understand how well they adhere to, or violate, the Empirically-Derived Principles for Designing Products with Flexibility for Future Evolution introduced by Tilstra et al.