Conventional VAR compensation devices such as capacitor banks and synchronous condensers, after long periods of service, have become aged and less effective to satisfy stringent requirement of short-term voltage stability in high-level wind power penetrated power systems. STATCOMs with a rapid and dynamic reactive power support capability can be an ideal alternative, when combined with a proper equipment retirement and upgrades scheme. This paper proposes a systematic approach for optimal dynamic VAR resource planning and upgrading for a power system with increased wind power penetration and equipment retirement. The problem is constituted by two parts which are aged equipment retirement and new equipment placement. A multi-objective optimization model is proposed to minimize three objectives: 1) the cost of retirement and upgrades, 2) the index of proximity to steady state voltage collapse, and 3) the index of transient voltage unaccepted performance. To simulate real-world operating situation, multiple contingencies and uncertain dynamic load models are taken into account. Furthermore, Low and High Voltage Ride Through abilities for wind farms are modeled. The proposed model is tested on the New England 39-bus test system.