Quaive is a Plone-based social community collaboration platform. This summmer we shipped Quaive 4, a major upgrade with a new notifications system. We are planning an even bigger feature upgrade for Quaive 5. This talk focuses on how it all hangs together: - design: how features can reinforce each other; - development: taming technical debt and maintaining forward momentum; - devops: platform architecture and deployment pipelines; - business: how to secure funding for maintenance & new feature development.