I\'m toying around with writing a random map generator, and am not quite sure how to randomly generate realistic landscapes. I\'m working with these sorts of local-scale map
You could start reading links here. I remember looking at much better document. Will post it if I find it (it was also based on L-systems).
But that's on the general side; on the particular problem you face I guess you should model it in terms of
The point is that even though you don't know how to construct the map with given properties, if you are able to evaluate the properties (clustering ratio; path niceness) and score on them you can then brute force or do some other problem space transversal.
If you still want to do generative approach then you will have to examine generative rules a bit closer; here's an idea that I would pursue