I'll use Winterhold as an example here since it's a small settlement. Let's start with The Frozen Hearth inn. If you stand in the inn and just observe for awhile, Dagur has four random conversation topics with his wife, Haran. These are:
1) A discussion of their mead supply.
2) Haran's dislike of her daughter playing a game called "Hunt the Elf" with the Jarl's son.
3) Haran's concern that Ranmir drinks too much, with Dagur responding that it's not their business to get involved.
4) A discussion of Jarl Korir, and his complaints of the inn's guests.
Dagur also has two conversations with Nelacar:
1) Nelacar asking Dagur if he heard any "loud explosions" last night.
2) Dagur asking Nelacar if he's had any trouble with other visitors to the inn.
When Birna (shopkeeper) gets off work, she'll enter the inn (around 8:30 ish) which should prompt to Ranmir to stand up and they'll have one of two (perhaps three, I can't recall) conversations about his binge drinking.
At the Jarl's Longhouse, Jarl Korir and Thaena will piss and moan about how Dagur is allowing Nelacar to reside at the inn. The Jarl will also talk to his son about how "bad" the mages at the college are, with the Jarl's son saying "I hate them!" to which the Jarl responds "That's my boy!"
Finally over at Kraldar's house, Kraldor will ask Thonjolf if there's anything of interest happening lately to which Thonjolf will reply in the negative.
So for those of you reading this, perhaps you could indulge me and head on over to Winterhold on your current character and let me know if you see any of these conversations taking place?