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The complexity of power systems has increased in recent years due to the operation of existing transmission lines closer to their limits, using flexible AC transmission system devices (FACTS), and also due to the increased penetration of new types of generators that have more intermittent characteristics and lower inertial response, such as wind generators. This changing nature of a power system has considerable effect on its dynamic behaviours resulting in power swings, dynamic interactions between different power system devices and less synchronized coupling. This paper presents some analyses of this changing nature of power systems and their dynamic behaviours to identify critical issues that limit the large-scale integration of wind generators and FACTS devices. In addition, this paper addresses some general concerns towards high compensations in different grid topologies. The studies in this paper are conducted on the New England and New York power system model under both small and large disturbances. From the analyses, it can be concluded that high compensation can reduce the security limits under certain operating conditions, and the modes related to operating slip and shaft stiffness are critical as they may limit the large-scale integration of wind generation.