Electric grid operators have proven very adept at handling complexity and uncertainty. However, as uncertainty and variability continue to grow with increasing introduction of renewable generation, distributed energy resources, retirement of dispatchable generation, and occurrence of more frequent and historic weather events, operators will expericence new workload and challenging decision scenarios. New types of resources and technology, like dynamic line ratings, are being introduced to the system to attempt to address transmission congestion, often without fully considering the operator. When integrating a novel technology, the concept of operations is commonly overlooked during the development phase, and is often only defined during, or even after the actual implementation. This paper provides an example of defining a concept of operations for a case study of a dynamic line rating (DLR) implementation and its integration with offshore wind generation (OSW) to consider risk and benefits of DLR due to weather forecast uncertainty. The analysis results offer insights into DLR and OSW forecast uncertainties, establishing a baseline for conducting studies on the acceptable level of uncertainty for operators. For implementation of future advanced technologies, researchers can utilize similar analyses to understand the effectiveness and potential impacts of these technologies on control room operations.