We are on the threshold of a new era of sustainable exploration and development of space. New Launch vehicles and programs such as NASA's Artemis and Lunar Gateway will change space technology and the stakes for space systems as we know them. As a result of these and other transformative changes, opportunities to launch and operate new space vehicle architectures will be unprecedented. To this end, this dissertation provides three foundational studies intended to impart rigor and systems thinking to the development and planning efforts of next-generation space projects. 1) Navigating the Policy Compliance Roadmap for Small SatellitesThis study explores USA space policy and regulatory processes and how they apply to satellites not fitting the typical mold of traditional missions. It lays out a systematic way forward for small satellite mission developers and managers to navigate the approval quagmire for individual spacecraft on multi-payload launches. It also puts forth ways for approving new and expected future mission architectures and technologies. Additionally, areas are identified where there are policy and regulation gaps and "gray areas" to prepare developers and inform other stakeholders of potential issues. 2) Lessons Learned from the First Generation Interplanetary CubeSatsThis study analyzes information gathered from the first sixteen interplanetary CubeSats and the unique difficulties faced by this mission type. Solutions to the specific development problems and general observations on the engineering and programmatic challenges faced by this mission type were solicited from previous mission developers and documented. From this, development approaches are proposed to lower risk and costs for future mission developers and stakeholders. 3) Evaluating Mars Rotorcraft Development InvestmentsRotorcraft can offer a new paradigm for Martian surface and atmospheric exploration missions. This study was conducted to enable stakeholders to evaluate competing research and development efforts for Mars Rotorcraft technologies. Not only for their estimated costs and system performance but also for their long-term improvement potential in the context of other ongoing developments. It does this by establishing critical metrics and relationship models for evaluating rotorcraft system and subsystem performance. Then the alignment of potential developments to the broader NASA technology goals and ways to estimate returns on investments were established.