In large procedural landscape games, the land seems dull, but that's probably because the real world is largely dull, with only limited places where the scenery is dramatic or tactical.

Looking at world generation from this point of view, a landscape generator for a game (that is, not for the sake of scenery, but for the sake of gameplay) needs to not follow the rules of landscaping, but instead some rules married to the expectations of the gamer. For example, there could be a choke point / route generator that creates hills ravines, rivers and mountains between cities, rather than the natural way cities arise, scattered on the land based on resources or conditions generated by the mountains and rainfall patterns.

Is there any existing work being done like this? Start with cities or population centres and then add in terrain afterwards?

The reason I'm asking is that I'd previously pondered taking existing maps from fantasy fiction (my own and others), putting the information into the system as a base point, and then generating a good world to play in from it. This seems covered by existing technology, that is, where the designer puts in all the necessary information such as the city populations, resources, biomes, road networks and rivers, then allows the PCG fill in the gaps.

But now I'm wondering if it may be possible to have a content generator generate also the overall design. Generate the cities and population centres, balancing them so that there is a natural seeming need of commerce, then generate the positions and connectivity, then from the type of city produce the list of necessary resources that must be nearby, and only then, maybe given some rules on how to make the journey between cities both believable and interesting, generate the final content including the roads, the choke points, the bridges and tunnels, ferries and the terrain including the biomes and coastline necessary.

If this has been done before, I'd like to know, and would like to know what went wrong, and what went right.