Dynamic thermal rating allows transformers to operate beyond the nameplate rating according to the actual weather and loading conditions. This paper proposes a methodology to improve the application of this technology in the design of new transformers or in the operation of existing transformers connected to wind farms by accurately predicting their load profiles, accounting for the influence of wake effect and turbine availability. Specifically, the variation of turbine availability due to the intermittent wind is considered in the load profile estimation. Additionally, a correction method, which can be incorporated into any wake model, is proposed to improve the accuracy of wake loss computation. A case study shows that the wake effect and the changing turbine availability shorten the time that the transformers maintain at full load, thereby reducing the aging rate of the wind farm export transformers. The findings suggest that considering these two factors in the DTR application can benefit the longevity and efficiency of wind farm exported transformers.