Accurate assessment of spheno-occipital synchondrosis (SOS) maturation is a key indicator of craniofacial growth and a critical determinant for orthodontic and surgical timing. However, SOS staging from cone-beam CT (CBCT) relies on subtle, continuously evolving morphological cues, leading to high inter-observer variability and poor reproducibility, especially at transitional fusion stages. We frame SOS assessment as a fine-grained visual recognition problem and propose a progressive representation-learning framework that explicitly mirrors how expert clinicians reason about synchondral fusion: from coarse anatomical structure to increasingly subtle patterns of closure. Rather than training a full-capacity network end-to-end, we sequentially grow the model by activating deeper blocks over time, allowing early layers to first encode stable cranial base morphology before higher-level layers specialize in discriminating adjacent maturation stages. This yields a curriculum over network depth that aligns deep feature learning with the biological continuum of SOS fusion. Extensive experiments across convolutional and transformer-based architectures show that this expert-inspired training strategy produces more stable optimization and consistently higher accuracy than standard training, particularly for ambiguous intermediate stages. Importantly, these gains are achieved without changing network architectures or loss functions, demonstrating that training dynamics alone can substantially improve anatomical representation learning. The proposed framework establishes a principled link between expert dental intuition and deep visual representations, enabling robust, data-efficient SOS staging from CBCT and offering a general strategy for modeling other continuous biological processes in medical imaging.