This paper presents a comparative analysis of deep learning strategies for detecting hypertensive retinopathy from fundus images, a central task in the HRDC challenge~\cite{qian2025hrdc}. We investigate three distinct approaches: a custom CNN, a suite of pre-trained transformer-based models, and an AutoML solution. Our findings reveal a stark, architecture-dependent response to data augmentation. Augmentation significantly boosts the performance of pure Vision Transformers (ViTs), which we hypothesize is due to their weaker inductive biases, forcing them to learn robust spatial and structural features. Conversely, the same augmentation strategy degrades the performance of hybrid ViT-CNN models, whose stronger, pre-existing biases from the CNN component may be "confused" by the transformations. We show that smaller patch sizes (ViT-B/8) excel on augmented data, enhancing fine-grained detail capture. Furthermore, we demonstrate that a powerful self-supervised model like DINOv2 fails on the original, limited dataset but is "rescued" by augmentation, highlighting the critical need for data diversity to unlock its potential. Preliminary tests with a ViT-Large model show poor performance, underscoring the risk of using overly-capacitive models on specialized, smaller datasets. This work provides critical insights into the interplay between model architecture, data augmentation, and dataset size for medical image classification.