Modern aerospace systems rely heavily on legacy platforms and their derivatives. Historical examples show that after a vehicle design is frozen and delivered to a customer, successive upgrades are often made to fulfill changing requirements. Current practices of adapting to emerging needs with derivative designs, retrofits, and upgrades are often reactive and ad-hoc, resulting in performance and cost penalties. Recent DoD acquisition policies have addressed this problem by establishing a general paradigm for design for lifelong evolution. However, there is a need for a unified, practical design approach that considers the lifetime evolution of an aircraft concept by incorporating future requirements and technologies. This research proposes a systematic approach with which the decision makers can evaluate the value and risk of a new aircraft development program, including potential derivative development opportunities. The proposed Evaluation of Lifelong Vehicle Evolution (EvoLVE) method is a two- or multi-stage representation of the aircraft design process that accommodates initial development phases as well as follow-on phases. One of the key elements of this method is the Stochastic Programming with Recourse (SPR) technique, which accounts for uncertainties associated with future requirements. The remedial approach of SPR in its two distinctive problem-solving steps is well suited to aircraft design problems where derivatives, retrofits, and upgrades have been used to fix designs that were once but no longer optimal. The solution approach of SPR is complemented by the Risk-Averse Strategy Selection (RASS) technique to gauge risk associated with vehicle evolution options. In the absence of a full description of the random space, a scenario-based approach captures the randomness with a few probable scenarios and reveals implications of different future events. Last, an interactive framework for decision-making support allows simultaneous navigation of the current and future design space with a greater degree of freedom. A cantilevered beam design problem was set up and solved using the SPR technique to showcase its application to an engineering design setting. The full EvoLVE method was conducted on a notional multi-role fighter based on the F/A-18 Hornet.