The possibility of converting overhead distribution facilities to underground has been increasingly of interest after the 2004-2005 hurricane season. It is well known that overhead-to-underground conversions are costly, but no consistent quantitative cost-benefit analysis approach has yet been available. This paper proposes a framework to quantitatively investigate the implications of overhead-to-underground conversions, in an attempt to add consistency, rigor, and thoroughness to these types of analyses. This framework incorporates hurricane simulation, damage estimation, post-hurricane restoration simulation, and cost-benefit analysis to assess the incremental or avoided costs by the conversion. The framework is also able to provide insights into how different variables affect the costs and the benefits of the conversions. Currently the parameters are customized for Florida, but the methodology is widely applicable.