The conditional min-entropy, discussed e.g. in these notes by Watrous, as well as in this other post, can be defined as $$\mathsf{H}_{\rm min }(\mathsf{X} \mid \mathsf{Y})_{\rho}\equiv -\inf _{\sigma \in \mathsf{D}(\mathcal Y)} \mathsf{D}_{\rm max }\left(\rho \| \mathbb{1}_{\cal X} \otimes \sigma\right), \\ \mathsf D_{\max }(\rho \| Q)\equiv \inf \left\{\lambda \in \mathbb{R}: \rho \leq 2^{\lambda} Q\right\}. $$ Among other things, it can be given a rather direct operational interpretation, at least for classical-quantum states $\rho=\sum_a p_a |a\rangle\!\langle a|\otimes\xi_a$, as $-\log p_{\rm opt}$, with $p_{\rm opt}$ the optimal guessing probability of discriminating between the elements of the ensemble $a\mapsto (p_a,\xi_a)$.
What do these quantities look like for diagonal matrices? For the relative min-entropy I would get $$\mathsf D_{\rm max}(P\|Q)=\max_i \log\frac{p_i}{q_i},$$ with $p_i\equiv P_{ii}$ and $q_i\equiv Q_{ii}$. I'm however less sure about how to compute $\mathsf H_{\rm min}(\mathsf X|\mathsf Y)_\rho$. The problem being that the minimisation is defined over all possible states, not just diagonal ones. To get a quantity which can be seamlessly applied also to classical distributions, I would guess that the $\inf$ should be saturated by diagonal states $\sigma$. Even assuming this to be the case (which would need to be shown anyway), I'd get $$\mathsf H_{\rm min}(\mathsf X|\mathsf Y)_P = -\inf_{\vec q}\log \max_{a,b} \frac{p_{a,b}}{q_b},$$ where $P$ is some bipartite probability distribution, and the $\inf$ is taken over all probability distributions $\vec q$ on the second system.
Assuming these expressions are correct in the first place, is there a simpler approach leading to nicer expressions? Or let's say, expressions that would seem more natural in a purely classical context.