Investments in power generation assets are multi-year projects with high costs and multi-decade lifetimes. Since market circumstances can significantly change over time, investments into such assets are risky and require structured decision-support systems. Investment decisions and dispatch in electricity spot markets are connected, thus requiring anticipation of expected market outcomes. This strategic situation can be described as a bilevel optimization problem. At the upper level, an investor decides on investments while anticipating the market results. At the lower level, a market operator maximizes welfare given consumer demand and installed generation assets as well as producer price bids. In this paper, we formulate this problem as a mathematical program with equilibrium constraints (MPEC). We consider this model to include a dynamic, rolling-horizon optimization. This structure splits the investment process into multiple stages, allowing the modification of wait-and-see decisions. This is a realistic representation of actors making their decision under imperfect information and has the advantage of allowing the players to adjust their data in between rolls. This more closely models real-world decision-making and allows for learning and other feedback in between rolls. The rolling-horizon formulation also has the beneficial byproduct of computational advantage over a fixed-horizon stochastic optimization formulation since smaller problems are solved and we provide supporting numerical results to this point.