Based on interviews with 20+ engineering teams, this guide examines when Backstage (Spotify's open-source developer portal framework) makes sense for organizations. Backstage works best for teams with 30+ engineers, multiple microservices, and 3-5 dedicated maintainers who can handle React/TypeScript. The framework isn't free despite being open-source—expect $380-650k annually for DIY implementation versus $84k for managed alternatives. Common pitfalls include underestimating frontend skill requirements, forcing 100% adoption, and lacking executive sponsorship. Success requires focusing on specific pain points (onboarding, service scaffolding, documentation), measuring ROI through metrics like time-to-first-PR and MTTR, and treating the portal as an internal product with iterative rollouts.