This paper attempts to characterize the kinds of physical scenarios in which an online learning-based cognitive radar is expected to reliably outperform a fixed rule-based waveform selection strategy, as well as the converse. We seek general insights through an examination of two decision-making scenarios, namely dynamic spectrum access and multiple-target tracking. The radar scene is characterized by inducing a state-space model and examining the structure of its underlying Markov state transition matrix, in terms of entropy rate and diagonality. It is found that entropy rate is a strong predictor of online learning-based waveform selection, while diagonality is a better predictor of fixed rule-based waveform selection. We show that these measures can be used to predict first and second-order stochastic dominance relationships, which can allow system designers to make use of simple decision rules instead of more cumbersome learning approaches under certain conditions. We validate our findings through numerical results for each application and provide guidelines for future implementations.