Migrating a Node.js project from version 14 to 18 can be approached using different workflows, each with its strengths and weaknesses. A hands-on method with an AI assistant, such as Claude Code, involves iterative code modifications where the AI provides context-aware suggestions directly in the files, addressing issues like ESM import mismatches and OpenSSL deprecations as they arise. However, this approach lacks a centralized record of changes, making it less suitable for team environments. In contrast, using a spec-driven workflow with Aviator Runbooks provides a structured, repeatable plan with a clear sequence of steps, capturing every change in a runbook log. This method offers transparency and traceability, facilitating team collaboration and allowing for predictable upgrades across multiple repositories. While both methods successfully update dependencies and resolve typical migration challenges, Aviator’s approach emphasizes process consistency and documentation, making it ideal for teams requiring a documented upgrade path.