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The demand for energy in developing countries of the Caribbean region is increasing. Local environmental policy influence energy production and consumption, while the integration of renewable energy sources must reliably satisfy this increasing load demand economically. This paper uses auto-regressive modeling to assess the adequacy of potential sites for wind power generation. Monte Carlo Simulation was employed to evaluate well-being indices for the combination of wind and conventional power generation. Two sites in Trinidad and Tobago were used as case studies for the outlined methodology. The results illustrate the methodology employed should be applied to sites with relatively more favourable conditions for economic feasibility of wind power generation.