The biggest pain points for startup devs managing cloud deployments revolve around dependency issues with popular CI tooling, being stuck with non-portable cloud solutions, and administrative overhead with complex systems like Kubernetes. Key recommendations include building and testing on standalone workstations, keeping deployments simple with AWS services like ECR and ECS, ensuring container portability, careful management of persistent storage, and financial vigilance to avoid excessive costs. Prioritize simplicity and scalability over complex microservices architectures.