Cross-asset optimization decision models and tools can help Canadian municipalities build optimal programs and identify optimal budget allocation and investment strategies across different asset systems. This paper describes a multi-objective optimization methodology and a software solution to support the development of optimal portfolio programs. The proposed methodology supports program development decisions through quantitative analysis of investment and strategy trade-offs. The optimization model can efficiently evaluate trade-offs within and across different asset systems to optimize project selections for each year in the planning horizon. The proposed methodology follows a two-step approach, where programs are first optimized for individual asset systems under a range of scenarios, and then then identifying optimal budget allocation and select optimal projects across different asset systems to maximize portfolio performance. The presentation presents four case studies to develop an optimal 10-year cross-asset program for four Canadian cities.