This paper investigates the applicability of offline-first strategies for workload placement in multi-cloud environments, focusing on integrating on-premise resources. The authors analyze the evolution from traditional on-premise IT infrastructures to hybrid and multi-cloud models, highlighting the growing complexity of interoperability, cost management, and vendor lock-in. Sky Computing is presented as a paradigm that abstracts cloud resources across providers via an intercloud broker, enabling dynamic, vendor-agnostic resource allocation and service migration. The paper explores the challenges of secure connectivity, data gravity, and latency in distributed environments. It discusses the role of Software Defined Networking (SDN) and Secure Access Service Edge (SASE) in facilitating seamless and secure integration of on-premise and cloud workloads. A key contribution is introducing the SKY CONTROL framework, designed to address the specific needs of small and medium-sized enterprises (SMEs) by providing cost and risk management, infrastructure transparency, and support for geographic workload distribution. The study concludes that Sky Computing and offline-first strategies offer significant potential for enhancing flexibility and resilience in multi-cloud environments. However, further research is needed to develop standardized methodologies for workload placement and address open interoperability and security challenges.