We show that constraints on scalar field potentials and towers of light massive states in asymptotic limits of scalar field space (as posited by the de Sitter Conjecture and the Swampland Distance Conjecture, respectively) are correlated with the prospects for defining asymptotic observables in expanding FRW cosmologies. The observations of a "census taker" in an eternally inflating cosmology are further related to the question of whether certain domain walls satisfy a version of the Weak Gravity Conjecture. This suggests that answers to fundamental questions about asymptotic observables in cosmology could help shed light on the Swampland program, and vice versa.