The democratization of open-source Large Language Models (LLMs) allows users to fine-tune and deploy models on local infrastructure but exposes them to a First Mile deployment landscape. Unlike black-box API consumption, the reliability of user-managed orchestration remains a critical blind spot. To bridge this gap, we conduct the first large-scale empirical study of 705 real-world failures from the open-source DeepSeek, Llama, and Qwen ecosystems. Our analysis reveals a paradigm shift: white-box orchestration relocates the reliability bottleneck from model algorithmic defects to the systemic fragility of the deployment stack. We identify three key phenomena: (1) Diagnostic Divergence: runtime crashes distinctively signal infrastructure friction, whereas incorrect functionality serves as a signature for internal tokenizer defects. (2) Systemic Homogeneity: Root causes converge across divergent series, confirming reliability barriers are inherent to the shared ecosystem rather than specific architectures. (3) Lifecycle Escalation: Barriers escalate from intrinsic configuration struggles during fine-tuning to compounded environmental incompatibilities during inference. Supported by our publicly available dataset, these insights provide actionable guidance for enhancing the reliability of the LLM landscape.