In this article, we explore the commercial realities shaping the adoption of Structural Health Monitoring (SHM) across infrastructure projects. While SHM is often discussed in terms of advanced sensors and data-driven engineering, our conversation with Mr. Bhobe reveals that its success is far more dependent on how systems are procured, packaged, and funded. From line-item procurement and fragmented decision-making to installation-heavy deployment models, the article examines why many monitoring systems remain underutilized despite being technically capable. Ultimately, it reframes the core industry challenge: not whether monitoring technology works, but whether current commercial and operational structures allow it to deliver meaningful long-term engineering value.