1. What’s special about it?
2. What’s the weather like?
3. Who rules/makes decisions?
4. Okay, who really rules/makes decisions?
5. What’s their chief export? How do most of its non-merchant citizens make money?
6. What’s crime like?
7. What’s the law like?
8. Who can you ask about in town that everyone has some kind of rumor about?
9. Does the place have any holidays?
10. What’s the population like?
11. Is there diversity?
12. How does the place get along with neighboring settlements?
13. Where is the closest tavern? What is it called?
14. How do most people enter the settlement?
15. Is there a marketplace? A market day?
16. What kind of recurring troubles does the settlement have?
17. What happens if a character is caught committing a petty crime?
18. What happens if a character commits a murder? What if he/she is caught?
19. How do people talk here?
20. What/Who do people who live here believe in, religiously, for the most part?
If you have any suggestions for more questions, feel free to post them in the comments!