This study presents a multi-objective framework to evaluate the integration of distant wind farms with associated transmission network upgrades on optimal power system planning. The presented approach also extends the technique to include the consideration of energy limitations associated with the installed hydro generation facilities. This study attempts to emphasise on the reliability implications rather than the production cost evaluation aspects. The decision making is based on hierarchal level II (HL-II) Expected Energy Not Served as an entire power system reliability assurance, and capital cost plus annual operational cost as an economical index. Non-dominated Sorting Genetic Algorithm is adopted to achieve the Pareto front of the aforementioned multi-objective problem. A fuzzy satisfying method, designated as the distance metric, is used to represents a trade-off between different objectives. To numerically evaluate the efficiency of the proposed method, simulation results on three case studies are provided. In spite of huge computation burden at HL-II reliability assessment, the results indicate high efficiency of the proposed method.