We present ongoing work on annotating fine-grained semantic distinctions for circumstantial meanings, focusing on spatial expressions.We describe our theoretical background, and annotation process, as well as how we evaluate the results obtained.Using multiple independent annotations across the 3-million-token, genre-diverse Prague Dependency Treebank -Consolidated corpus of Czech data, we analyse inter-annotator agreement, recurrent disagreement patterns, and the limits of semantic categorization.Our results highlight the inherent vagueness of linguistic meaning.We also propose strategies for handling disagreement, such as weighted annotations, intermediate labels, and fuzzy labels that preserve annotation nuance.This work builds on the legacy of Petr Sgall and the Functional Generative Description theory that underpins the multi-layer form-meaning framework.