A self-education program probably isn't going to compete with the NCAA finals or the lastest version of Law and Order or CSI, but I think the world would be a better place if more people took an interest in improving their minds.
There are far too many cities, towns, and communities in the world to make a comprehensive listing, and I have not yet found a source that gives them a significant treatment, although there may be one, or more, buried somewhere in the anthropological literature. The best approach I have been able to find is an indirect one.
Individuals who are connected to a city, by either having lived in one or visited it provide only a sample of what can be learned about it. A city's size or population is only a small step in learning about it, although quite a few facts can be guessed from its size and density of population. Large cities are more complex than small ones, and the complexity goes up faster than the population. The geography of a city site may tell a great deal about it. The buildings, streets, and other structures of a city are generally more enduring than particular individuals, and can be examined using methods of culture. The cultural institutions of a city are usually embodied in such buildings, and the size, prominence, and state of buildings are important indicators of the past or present importance. For example, there are churches, schools, government buildings, business and office buildings, and houses. These may or may not reflect ethnic groups and social classes, and may be easier to understand with history of the city or provide clues to the history of a city. Very few cities have existed throughout history: they tend to grow and decline, although in modern times, as the world's population has grown, more people have become concentrated in cities and there has overall been more growth than decline.
As an exercise, an excellent way to begin a self-education program is to begin with your own neighborhood and city. At some point, I may provide a sample analysis to suggest how the various subjects I have discussed so far can contribute.