Jeddah (Jiddah), Saudi Arabia

With a population of 4.7 million, Jeddah is a sprawling, unwieldy metropolis that requires careful planning for any would-be expat. The long-promised Jeddah Metro remains stuck in the planning stages, a victim of shifting national priorities and budget constraints. Meanwhile, bureaucratic delays continue to be a persistent headache for residents and visitors alike.

While Jeddah positions itself as the commercial heart of Saudi Arabia, the city's infrastructure and development struggles to keep pace with its rapid growth. Reliable public transit remains elusive, and the scorching desert climate can be a grueling challenge for the uninitiated. Navigating Jeddah's complexities is not for the faint of heart.

This bustling Red Sea port may appeal to seasoned expats seeking business opportunities, but for the average American, the city's formidable logistical hurdles and cultural barriers make it a poor choice for a new start abroad.