First thing to keep in mind is the dice rating. I made a big deal about regularizing the way settlements and territories are rated by size in terms of dice because it lets us cover a lot of information with one simple stat. Hamlets get half a die, Villages get a full die, and we add 1d6 for each major size increase; that's the number of trades, and if we subtract 1d6, we get the number of NPCs per trade and the number of inns and taverns (and there will be half as many churches as inns+taverns.) Large and Small are now 1-point modifiers. That means we can practically reconstruct almost all the table entries for a settlement from a short line like "1d6 Large Village". Similarly, "1d6 Duchy" tells us how many towns are in the duchy, and if we subtract 1d6, the number of dice (in this case, 0) is the base number of cities, barring towns that get upgraded to city status.
We can characterize the feel of a town or kingdom as well. I once talked about labeling towns and NPCs as Villainous, Cruel, Grouchy, Petty, Pleasant, Compassionate, or Idealist, based on a reaction or loyalty roll. We can add that in front of the dice rating: "Grouchy 1d6 Large Village", "Villainous 2d6 Small Kingdom". Territories set the default character of their settlements; once you know a Barony is Pleasant, individual hamlets and villages will be off by 1 at most, so just roll a d4 and drop Pleasant to Petty on a 1 or increase it to Compassionate on a 4.
The main thing we want to know is what the main economic activity of a settlement or region is. The default is some kind of Farming for plains or hills, Hunting or Lumber for forrest, Fishing or Trade for settlements along the water, and Mining for those in the mountains. You can use a modification of the random name technique to come up with more specific ideas: roll 2d20 and 1d6, read left to right using the table in the Sybad post, and use that as an abbreviation of the name of some export or economic activity. We can record this two different ways:
- Insert the economic activity in between the size rating (and modifier) and the settlement/territory type. Example: "Grouchy 1d6 Large Farming Village"
- Add the name of the primary service for that economic activity. Example: "Grouchy 1d6 Large Village w/ Grain Mill"
Another thing we want to know is what's different about this village or this kingdom, compared to others of the same size and general economic activity. One way to handle this is use the 2d20+1d6 "abbreviation roll" to roll up the target of a locale's villainy, cruelty, compassion, or ideals. Another is to use a random encounter roll to determine what being in the area is the topic of conversation, devotion, awe, or fear. You could also use tables from something like the Judges Guild Ready Reference Sheets or Kellri's Encounter Reference to determine a unique structure in the center of town or in the capital city of a kingdom.
So, after you've picked or randomly generated a name, your "stat block" for a settlement is going to look something like:
Crudeville, Grouchy 1d6 Large Village w/ Grain Mill, favorite mayor recently diedAnd we can fill in more details when the players actually deal with Crudeville.