This work develops a method of quantifying the effect of adding meshed connections to radial network topologies used for offshore extraction. The method accounts for Capital Expenditures (CAPEX), Corrective maintenance (CM), losses and Expected Energy Not Transmitted (EENT). The stochastic nature of wind is also accounted for. The method is applied to a statistically significant randomly generated population of Offshore Wind Power Plant (OWPP) pairs. Analysis of both Medium Voltage (MV) and High Voltage (HV) bus meshing is performed. It is demonstrated that in the two OWPPs case meshed connections have a narrow but significant region of applicability. Further, the method is applied to a system of 6 wind farms and compared to the lowest cost radial connection, using a number of different planning horizons. It is shown that the optimal radial topology is no longer the clear choice as the development horizon increases.