Common upper limb peripheral artery diseases (PADs) are atherosclerosis, embolic diseases, and systemic diseases, which are often asymptomatic, and the narrowed arteries (stenosis) will gradually reduce blood flow in the right or left upper limbs. Upper extremity vascular disease (UEVD) and atherosclerosis are high-risk PADs for patients with Type 2 diabetes or with both diabetes and end-stage renal disease. For early UEVD detection, a fingertip-based, toe-based, or wrist-based photoplethysmography (PPG) tool is a simple and noninvasive measurement system for vital sign monitoring and healthcare applications. Based on time-domain PPG analysis, a Duffing–Holmes system with a master system and a slave system is used to extract self-synchronization dynamic errors, which can track the differences in PPG morphology (in amplitudes (systolic peak) and time delay (systolic peak to diastolic peak)) between healthy subjects and PAD patients. In the preliminary analysis, the self-synchronization dynamic errors can be used to evaluate risk levels based on the reflection index (RI), which includes normal condition, lower PAD, and higher PAD. Then, a one-dimensional convolutional neural network is established as a multilayer classifier for automatic UEVD screening. The experimental results indicated that the self-synchronization dynamic errors have a positive correlation with the RI (R2 = 0.6694). The K-fold cross-validation is used to verify the performance of the proposed classifier with recall (%), precision (%), accuracy (%), and F1 score.