We begin by revisiting a paper of Erdős and Fishburn, which posed the following question: given $k\in \mathbb{N}$, what is the maximum number of points in a plane that determine at most $k$ distinct distances, and can such optimal configurations be classified? We rigorously verify claims made in remarks in that paper, including the fact that the vertices of a regular polygon, with or without an additional point at the center, cannot form an optimal configuration for any $k\geq 7$. Further, we investigate configurations in both triangular and rectangular lattices studied by Erdős and Fishburn. We collect a large amount of data related to these and other configurations, some of which correct errors in the original paper, and we use that data and additional analysis to provide explanations and make conjectures.