This is an analysis of some of the common models of healthcare systems including their structure, advantages, shortcomings, and challenges. The various models of healthcare delivery systems worldwide are examined with special focus on the United States and Cuba, another Caribbean country. Particular emphasis is placed on challenges encountered by developing countries in general and Trinidad and Tobago in particular. This twin island state is used as an example of a democratic developing country in transition to a modern economy, and its healthcare system is considered in detail against this background. The study came up with a set of promising proposals to meet the challenges of healthcare provision in this setting.