Autonomous drones offer transformative potential for inspecting above-ground port infrastructure by improving efficiency, safety, and cost-effectiveness. However, their adoption in Germany faces legal, technical, and economic challenges. This paper analyzes the regulatory landscape, including VDI 6200, DIN 1076, and EASA guidelines, and integrates insights from expert interviews with port operators, engineers, and drone service providers. Key challenges include accessibility constraints, data-quality requirements, and the need for standardized inspection procedures. We present a structured framework to guide the implementation of autonomous drone inspections. While drones enable access to hard-to-reach areas and reduce human risk, their deployment requires significant investment and adaptation of existing processes. The study highlights opportunities for long-term cost savings through predictive maintenance and early damage detection but also identifies barriers such as regulatory ambiguity and high initial costs. By synthesizing legal, technical, and economic perspectives, this paper provides a roadmap for stakeholders to navigate the transition toward autonomous inspections. The findings underscore the need for clearer regulations and financial support, particularly for smaller ports, while offering actionable insights for policymakers and practitioners aiming to modernize inspection practices.