The fidelity-based smooth min-relative entropy is a distinguishability measure that has appeared in a variety of contexts in prior work on quantum information, including resource theories like thermodynamics and coherence. Here we provide a comprehensive study of this quantity. First we prove that it satisfies several basic properties, including the data-processing inequality. We also establish connections between the fidelity-based smooth min-relative entropy and other widely used information-theoretic quantities, including smooth min-relative entropy and smooth sandwiched Rényi relative entropy, of which the sandwiched Rényi relative entropy and smooth max-relative entropy are special cases. After that, we use these connections to establish the second-order asymptotics of the fidelity-based smooth min-relative entropy and all smooth sandwiched Rényi relative entropies, finding that the first-order term is the quantum relative entropy and the second-order term involves the quantum relative entropy variance. Utilizing the properties derived, we also show how the fidelity-based smooth min-relative entropy provides one-shot bounds for operational tasks in general resource theories in which the target state is mixed, with a particular example being randomness distillation. The above observations then lead to second-order expansions of the upper bounds on distillable randomness, as well as the precise second-order asymptotics of the distillable randomness of particular classical-quantum states. Finally, we establish semi-definite programs for smooth max-relative entropy and smooth conditional min-entropy, as well as a bilinear program for the fidelity-based smooth min-relative entropy, which we subsequently use to explore the tightness of a bound relating the last to the first.