One-dimensional orderings of spatial entities have been researched in many contexts, e.g. spatial indexing structures or visualizations for spatiotemporal trend analysis. While plenty of studies have been conducted to evaluate orderings of point-based data, polygonal shapes, despite their different topological properties, have received less attention. Existing measures to quantify errors in projections or orderings suffer from generic neighborhood definitions and over-simplification of distances when applied to polygonal data. In this work, we address these shortcomings by introducing measures that adapt to a varying neighborhood size depending on the number of contiguous neighbors and thus, address the limitations of existing measures for polygonal shapes. To guide experts in determining a suitable ordering, we propose a user-steerable visual analytics prototype capable of locally and globally inspecting ordering errors, investigating the impact of geographic obstacles, and comparing ordering strategies using our measures. We demonstrate the effectiveness of our approach through a use case and conducted an expert study with 8 data scientists as a qualitative evaluation of our approach. Our results show that users are capable of identifying ordering errors, comparing ordering strategies on a global and local scale, as well as assessing the impact of semantically relevant geographic obstacles.