For example, if I chose a random town from history, why did its inhabitants come there? Where do they get their food/water/goods/whatever? What was their wealth? How had that changed through its history?
When I read the history of a particular city on wikipedia, there seem to be trends like "settled because of some natural feature, grew because of something else, exports this and that." When I drive through towns in the middle of nowhere, I'm curious "What do people do here? How do they get the things they need and not lose money?"
I guess the question boils down to the history of "What was life like here and why?" on personal and economic levels. I get that it's an amazingly broad question, so I'd love to learn some of the general themes.
I don't even know what this is called, but I'd love to read some fun pop history/pop economics book to get insight into it.
Plenty of fields study that question: Why did people settle here? As an archaeologist with an emphasis on geography and urbanism, it's actually one of my main questions. Never in any of these studies, though, are we looking for general trends. These "trends," it turns out, are fairly obvious. The same things are good for a city no matter where you live: fresh water, arable land, pasture land, access to transport, protection from elements/enemies, etc. An ideal city would have all of these, but unfortunately these have trade offs. The best place to graze llama herds is not going to be the best place to plant potatoes, and the best place for your potatoes is not going be defensible should someone want to steal your potatoes.
What's actually interesting and worth studying is the trade-offs people made to prioritize one of these over another. There's a huge diversity or such choices even within a single area. Take the Andes. The imperialistic Huari and Inca created evenly dispersed settlements to enforce their political control over areas, placing them on main causeways or in the middle of conquered territory. Chavin de Huantar, the center of the first major pan-Andead culture, was built in a valley basin, difficult to reach but at the confluence of two rivers, a place of utility and symbolic importance. Later Recuay towns in the same region are built on cliff sides and mountain peaks, defensible positions with fortifications that correspond with the numerous warriors depicted in their art. We see settlements pop up around Lake Titicaca at convenient shipping ports.
When we ask why people might live somewhere, we're not looking for general trends. It sounds lame, but those trend are usually pretty obvious. It's the specific details that are interesting, the ones that make each city or culture unique.
And I don't know how to get rid of that "Urbanism" flair that popped on when I submitted this question.