Electric grid operators are adept at handling complexity and uncertainty. However, with increasing introduction of renewable generation, distributed energy resources, and more frequent severe weather events, operators will experience new workload and challenging decision scenarios. This paper quantifies risks and benefits from an operator’s perspective of introducing weather based forecast Dynamic Line Ratings (DLR) using variable wind conditions in addition to ambient temperature to relieve transmission congestion and facilitating more offshore wind (OSW). A concept of operations (CONOPS) applied to a forecast DLR implementation and its integration with OSW is defined. A method for evaluating tradeoffs of derating to make the rating more conservative but decreasing the benefit was developed and applied to a case study for two existing overhead transmission lines on Long Island, New York. The CONOPS uses historical day-ahead and hour-ahead High Resolution Rapid Refresh weather forecasts and weather station data to support planning and real-time operations. The analysis determines the risk of downgrades in real-time operational rating compared to the forecast and quantifies the frequency and severity of lastminute downgrades. The risk is compared against the benefits in increased capacity to provide insights on the additional amount of uncertainty DLR and OSW will add to the operator’s workload.