As official public records of inventions, patents provide an understanding of technological trends across the competitive landscape of various industries. However, traditional manual analysis methods have become increasingly inadequate due to the rapid expansion of patent information and its unstructured nature. This paper contributes an original approach to enhance the understanding of patent data, with connected vehicle (CV) patents serving as the case study. Using free, open-source natural language processing (NLP) libraries, the author introduces a novel metric to quantify the alignment of classifications by a subject matter expert (SME) and using machine learning (ML) methods. The metric is a composite index that includes a purity factor, evaluating the average ML conformity across SME classifications, and a dispersion factor, assessing the distribution of ML assigned topics across these classifications. This dual-factor approach, labeled the H-index, quantifies the alignment of ML models with SME understanding in the range of zero to unity. The workflow utilizes an exhaustive combination of state-of-the-art tokenizers, normalizers, vectorizers, and topic modelers to identify the best NLP pipeline for ML model optimization. The study offers manifold visualizations to provide an intuitive understanding of the areas where ML models align or diverge from SME classifications. The H-indices reveal that although ML models demonstrate considerable promise in patent analysis, the need for further advancements remain, especially in the domain of patent analysis.