For those who enjoy getting to really know their world, when starting a new adventurer or venturing to a new town, how much time do you tend to spend in a town getting to know the citizens and figure out if there is any interesting backstory to be found there? I feel like I always rush off when starting and I'm wondering if there's something I'm overlooking when interacting with the people living there. Any tips for getting more lore or just general excitement by talking to the townsfolk?
The most interesting people will be in taverns, keeps, and temples (and now in counting houses, guildhalls, and towers/manors). Or, I should say, these are the places where it is easiest to
find interesting people, as most of the folks there will be historical figures rather than individuals pulled from abstract population. They will actually have families and professions to talk about.
For lore, try talking to people about the structure you are in (assuming you're in one - tavern, temple, keep, etc.); they'll give you a random historical entry about the structure, usually when someone started ruling or working there. If you ask for directions to a town (including the one you're in), they'll also throw in a random fact about it. Of course, they have no way of knowing what facts are actually interesting, and what are meaningless (like, "in 324 Urist McFisherdwarf settled here"), so be prepared to ask over-and-over again if you want something juicy. Oh, you can also look at engravings on temple walls, which should have site-related historical entries.
But, in general, DF isn't forthcoming with its lore. Usually if I really want to get into the world, I'll read about its history in Legends Viewer. That can get you interested in certain places and people - like, if you want to track down a certain interesting person and talk to them, or visit the site of some important historical events.