In the second half of the twentieth century, phonological explorations of Ancient Greek and its dialectal diversity took two daring steps closely connected with the methodological advances in general linguistics. The first step was taken by Martín Ruipérez in 1956, who attempted to explain the sound changes in the vocalic systems of Attic and Boeotian by indicating what he thought to be the underlying structural causes of these changes. The second step was taken in 1984 by authors associated (at that time) with Université de Nancy, namely Monique Bile, Claude Brixhe and René Hodot, in a plea for proper incorporation of relevant sociolinguistic factors that could be held accountable for phonological changes in Ancient Greek. These attempts were deemed to be nothing short of methodological revolutions in the study of the development of Ancient Greek phonology and mark a decisive break with non–teleological description of the sound changes predominant in the nineteenth and first part of the twentieth century. The main aim of this paper is to evaluate the application and validity of these approaches in the study of Ancient Greek dialects in general, as well as through one specific example, namely the graphical unsteadiness of the representation of original inherited Proto-Greek /ē/ in Elean dialect.