VOLTAGE stability is a significant concern in power system operation. When a disturbance occurs, system is likely to experience a progressive voltage drop or rapid voltage collapse, which may result in cascading failures and even wide-spread blackouts. There are several severe blackouts that have been proven directly or indirectly related to voltage stability issues [1] and [2]. Regarding voltage stability enhancement concerns, seminal works like [3] , [4], [5] and [6] have proposed sizing and locating of VAR sources for reactive power compensation. However, limited by technological development and their original designing purposes, these designs are becoming less effective to handle dynamic VAR support nowadays. Today’s power systems are integrating more and more renewable energy resources, such as wind power and solar power, due to a purpose of reducing emissions and dependence on fossil fuels. Wind turbines are different from conventional synchronous generators; they are more unstable and sensitive to disturbance. In order to safely consume wind farms in traditional power systems, two security requirements called Low Voltage Ride Through (LVRT) and High Voltage Ride Through (HVRT), denoted as LH-VRT, need to be satisfied by the wind farms following a voltage disturbance [7]. In [8], LVRT has insightfully been an objective of dynamic VAR planning in a large-scale wind integrated system. The short-term voltage stability has become a critical threat to high-wind penetrated power systems. For example, in Sep 2016, a severe state-wide blackout event occurred in South Australia (SA), and one key driven-force is that wind farms failed to successively ride through the transient voltage dip [9], [10]. It is expected that the SA system will integrate more renewable energy by 2030. In such plan, the system inertia is expected to decrease continuously, which manifests the importance and necessity of an effective dynamic VAR support. In general, with further development of renewable energy, these issues might become increasingly important and urgent, which would be beyond what current static VAR devices such as capacitor banks are capable of. Meanwhile, some equipment requires major overhauls even retirement, which would be perfect timing to schedule upgrades. For VAR devices upgrades, planners should consider static compensator (STATCOM) with faster and more adequate reactive power compensation capabilities than the current devices have as an alternative, involving the retirement planning of aged equipment. Equipment aging is a significant problem in power systems. However, the existing methods of quantifying the uncertainty of failures are not developed enough to estimate potential losses precisely [11]. Retirement date approximation requires an enormous amount of historical data to determine a comparatively precise retirement date [12].