The present disclosure is directed to systems and methods for optimizing power output of a wind farm. The method includes determining baseline loading condition(s) for wind turbines of the wind farm and defining a baseline threshold value for the load sensors. Another step includes identifying at least one wind turbine having at least one load sensor operating below the baseline threshold value. An upgrade is then provided to the identified wind turbine. In response to the upgrade, the method includes determining whether the load sensor of the identified wind turbine continues to operate below the baseline threshold value. The method also includes classifying an additional load sensor(s) of an additional wind turbine with respect to the load sensor of the identified wind turbine to determine whether to provide the additional wind turbine with the upgrade.