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The target of this work is the determination of the optimal solution in transmission expansion planning in the particular case of isolated systems involving dc interconnections. Therefore special attention is given to dc-links modelling aspects for steady state analysis, as well as security constraints relevant to small sized systems operation. Therein lies the first contribution of this work, namely in the incorporation of operating reserve related considerations and simplified dc-links models in isolated systems planning. The proposed method combines a Monte-Carlo simulation, which enables the probabilistic assessment of power system operation, with an adaptive enumeration technique which recurrently determines and evaluates investment scenarios of interest, based on suitable probabilistic indices. This constitutes the second contribution of this work, as a map of all meaningful solutions to the planning problem may be generated, which in turn allows not only the determination of the optimal solution, but also the evaluation of the effects of over- or under-investment in certain parts of the grid.