The quarter system seems like a good start for larger population centers, but smaller areas are going to be mostly peasants and tradespeople, with zero to three of each of the other two quarters. So here's my current scheme:
- Hamlet: Has one service the local peasants need: a mill, for example. Has 1 to 3 other tradespeople or craftspeople. There's a maximum of 6 peasants in the area willing to serve as hirelings in mildly risky enterprises, but only 1-2 at a time; after the first expedition in an area, if a hireling has died, there will be 0 to 2 replacements available each week (half of d6 -2) until the limit is reached, after which the locale just can't spare any more of their friends, family, and neighbors.
- Small Village: Like a hamlet, but also has these services: a blacksmith, 1 to 3 other trades or crafts, a weekly market, and a tavern that can double as a place to crash for the night. There will be a religious leader of some kind, but not necessarily a formal church (services can be held in a common area.) There are 0 to 4 (d6-2) hirelings available each week; no max limit for the area, but use the number of deaths for a given expedition as a temporary penalty to the roll.
- Large Village: Has one locally-defined service like a hamlet, a blacksmith, 1d6+2 other tradespeople or craftspeople, a weekly market, a tavern PLUS an actual inn with rooms and a dedicated trader with a general store or trading post; there's probably also domesticated animals for sale, such as horses and mules. The religious leader will have an actual dedicated church or shrine to administer. There are 1 to 6 hirelings available each week, again with no max limit.
- Small Town: Like a large village, but with a daily market and 1 to 3 members of each common trade (apply penalties for the less common ones.) Instead of one blacksmith, one tavern, and one church, there will be 1 to 3 of each. There will be some kind of formal authority (mayor, town council, baron) and town guards or constables. Double the number of available hirelings.
Larger towns and cities can be extrapolated from the small town. The general idea I'm shooting for is just doing a sketch-map of a settlement's buildings, labeling any taverns, inns, market areas or trading post, and churches, and rolling for the rest as needed. All the dice rolls are based on d6/3, d6/2, d6-2, or multiples of d6, so it's easy improvise.