Linguistic changes often follow a cyclical path whereby the original formal expressions are worn down and first reinforced and later replaced by new ones. In how far such ‘micro-cycles’ conspire to engender ‘macro-cyclical’ developments in a language, and whether this can be measured quantitatively, is an under-researched question so far. The current project zooms in on three micro-cyclical changes in historical Chinese between c. 900-1900 CE, which are in different stages of advancement during this period, and aims to quantify the complex dynamics between them and morphological strategies at the macro-level: (i) the diachronic development of the disposal construction, (ii) the rise of postnominal localizers, and (iii) the evolution of modal markers. Based on the fine-grained annotation of degrees of grammaticality in a new corpus to be built as part of the project, we develop novel quantitative metrics linking such micro-changes to macro-cyclical developments in Mandarin Chinese, focussing on the often-neglected transition between stages. The hypothesis the project aims to test is that micro-cyclical changes lead to a macro-cyclical change, quantifiable as a.o. a rise in the morpheme-to-word and function-to-morpheme ratio. The system of annotation, informed by formal analysis, along with the corpus developed for this project may eventually be scaled for use in other projects, not only in Chinese historical linguistics.