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Operational planning of power systems, especially in terms of overall reliability and security, is a key issue in the smart grid development. Hence, it is necessary to develop new strategies to cope with increasing uncertainties arising from the fast changing ways power systems are being operated. This paper presents a comprehensive approach to determine an optimal transmission network expansion plan considering the enhancement of small-signal stability through wide-scale deployment of the existing and planned transmission system assets. The dynamic model of the transmission network operational planning (TNOP) is solved based on a combination of the Mean-Variance Mapping Optimization (MVMO), and the classic dynamic programming method embedded with a heuristic procedure. Besides, a probabilistic eigenanalysis-based recursive method is proposed to determine the optimal control strategies that are highly relevant to the enhancement of the system small-signal stability performance throughout the planning horizon. Numerical results demonstrate the viewpoint and the effectiveness of the proposed approach in providing optimal strategies of minimum cost while avoiding the instability risk associated to poorly damped low-frequency electromechanical oscillations.