This paper presents the design, development, and testing of an interactive planning tool for urban-wetland systems. The tool targets initial architectural and urban design stages, enabling a broader understanding of natural-urban synergies, ecosystem services, and sustainable systemic design strategies for water management, energy efficiency, on-site food production, community, coastal protection, and security. Targeting a test study site in Queensland, Australia, this paper aims to establish proof of concept for the tool algorithm used to calculate quantitative values for each sub-system and two novel system assessment criteria: ‘fair share’ (FS) and benefit cost (BC) ratio. The FS criterion is based on the permaculture FS ethical principle and tracks system diversity, resilience, and self-sustenance. The BC criterion builds on cost-benefit valuation methods but includes non-market values, providing a holistic assessment of system costs and benefits, including ecosystem services. Good practise (GP) and best practise (BP) design scenarios are developed for this study site and compared against a business-as-usual (BAU) case. Results demonstrate the relevance of FS and BC as assessment criteria to aid in the development of sustainable designs. Compared to the BAU scenario, the GP and BP scenario BC ratios increased 12 and 14 times, respectively. Yearly cost of living reductions for GP were equivalent to 26,990 AUD per site inhabitant, with BP resulting in a negative yearly cost of living (a yearly benefit equivalent to 6420 AUD per site inhabitant). The use of the FS and BC assessment criteria and tool highlights a potential new approach to planning and development processes, integrating aspects currently omitted within planning requirements and assessments.