This paper analyzes the fundamental trade-offs that occur in the co-design of orthogonal frequency-division multiplexing signals for both ranging (via time-of-arrival estimation) and communications. These trade-offs are quantified through the Shannon capacity bound, probability of outage, and the Ziv-Zakai bound on range estimation variance. Bounds are derived for signals experiencing frequency-selective Rayleigh block fading, accounting for the impact of limited channel knowledge and multi-antenna reception. Uncompensated carrier frequency offset and phase errors are also factored into the capacity bounds. Analysis based on the derived bounds demonstrates how Pareto-optimal design choices can be made to optimize the communication throughput, probability of outage, and ranging variance. Different signal design strategies are then analyzed, showing how Pareto-optimal design choices change depending on the channel.