Things I like to remember:
Villages, Settlements, Encampments

1. Many villages will have dogs, or early warning analogue animals. Consider an elven predilection of giant eagles (!), gnolls w/hyenadon (!). Approaching a random village could result in being attacked, killing one of their dogs considered a crime – at least a fine.

2. The current ‘mood’ of villagers can change the tenor of approach drastically. Are they hostile because they are harried by bandits and assume the worst of wandering adventurers? Are they in the middle of some twee celebration because the crop was good? There are stories of powers moving disguised though times of festival, if not all of the time.

3. On the subject of disguise, think about things that can polymorph. Some wizards, many demons and devils. Magic ogres, maybe powerful dragons (I’m not so much a fan of that). What do you want the odds to be in a population of 500, that there’s d12 dopplegangers or d6 ogre magi or something?

4. On the subject of disguise again (I know, a tangent…), how about the invisibles? Not so many of those. Nevertheless, let the sprites go invisible, and again with the magic ogres…

5. I like villages at a headcount of 100-500 (d6x100, 6 is 1), which is to say populations of that size. Nomadic cultures produce independent populations based on a dispersion percentage. Same with merchants. These tend to be much smaller on average, but the potential for truly huge hordes exists also.

6. I have always sucked at role-playing settlements, I prefer to make it more gamey. Rolling a d6 to determine how many internal divisions there are in a group if necessary. These divisions can be used to determine the temperament of the group as a whole. If they are balkanized (roll of 6) and antagonistic in general, the community will ‘feel’ different than if they are all ‘of one mind’ (roll of 1). The number of divisions could be used for patrol size, alignment division, kinda a lot of things on the fly.

7. I tend to think of village economies as being largely centered around one resource or feature for convenience. All villages will have some provision for water. D6, 6 is 1 yields an agricultural bump. Treat 6 as whatever you want, to increase the presence of resources, 5 for very developed locations.
A. <200 Agriculture
B. 200 Fortification
C. 250 Raw Material (wood, stone)
D. 300 Goods/Production/Manufacture
E. 350 Trade Route/Temple/Cultural Importance
F. 400 Agriculture & Fortification + one of C, D, or E
G. 450 Agriculture & Fortification + two of C, D, or E
H. 500 Agriculture & Fortification + C, D, and E

8. I like the idea that maybe 1 in 10 random villages are “class sanctuaries”. Instead of multiplying by 100, the die thrown for population is multiplied by a number keyed to the class in question.
A. X10 10-50 Clerics (potentially Cultist/Pilgrim, Paladin, Ranger, Assassin, Monk)
B. X10 10-50 Druids (potentially Cultist/Pilgrim, Berserker, examples of any other basic class, certainly animals)
C. X10 10-50 Fighters (potentially Bandit/Brigand, Berserker, Merchant)
D. X5 5-25 Magic Users (potentially anything!)
E. X5 5-25 Thieves (potentially Bandit/Brigand, Merchant, Assassin)
I like the idea – generates cleric temple & druid wyrd spots, wizard covens, thief gangs, strongpoints of arms. Could be used for quick & dirty level advancement, contacts, etc.