Modeling spaces and their relationships is at the core of syntactic analysis, including reach analysis. In a syntactic model, two spaces can be described as close together or far apart based on the directional distance between them. In this study, we compare three different ways of measuring directional distance—namely, by number of steps, by number of direction changes, and by angular deviation—in the context of accessibility and reach analysis. By graphically showing how choosing a different way of measuring directional distance can result in a different reach or accessibility pattern, we provide an intuitive understanding of the different natures of the syntactic measures. By demonstrating how the modeling conventions and the geometric composition of lines at a local scale can have a huge impact on the results of syntactic analysis at a larger scale, we call for more attention to the conventions and principles used for modeling street networks.