Decisions to invest in alternative intelligent transportation system (ITS) technologies are expected to increase in complexity, particularly with the introduction of connected vehicles (CV) and automated vehicles (AV) in the coming years. Traditional alternative analyses based on deterministic return on investment analysis are unable to capture the risks and uncertainties associated with the investment problem. In addition, these methods cannot account for agency preferences and constraints that cannot be converted to dollar values. This study utilizes a combination of a stochastic return on investment and a multi-criteria decision analysis method referred to as the Analytical Hierarchy Process (AHP) to select between ITS deployment alternatives considering emerging technologies. The approach is applied in a case study of the selection between using CV data and point detector data to support the freeway traffic data collection and monitoring service. The four objectives specified in the AHP analysis are providing the required functions, providing the required performance, minimizing the risks and constraints, and maximizing the return on investment. A stochastic return-on-investment analysis using a Monte Carlo simulation was used to calculate the return on investment values for input to the AHP method.