How do you people determine how many buildings will be in a city/town? Do you first decide on the population figure and then estimate the number of houses? Or do you create the map first and then figure out the population? Do you even consider this matter at all?

I'm personally haunted by these kind of questions. When I sit down to create a city map, I want the population density and the city size to be at least somewhat realistic. But the towns I want to map are not like modern ones; they are supposed to more or less resemble historical population centers of varying levels of technology. That makes things difficult to me. On one hand I don't think modern cities would make good examples. On the other hand I don't have enough knowledge about historical cities and their buildings.

Just how big were common houses in the past and how many people were living in one? How much did these things vary between different parts of the world and between different eras? I'm thinking that in general houses were smaller and that people were more densely crammed into them than in modern times. The houses may have been more closely packed too, with narrower streets between.

Having actual examples of preserved historical towns (so that the number and size of buildings can be known) with reliable information on their populations in the past would be invaluable help, but I'm not aware of any such examples.