Yeah. Cars take maintenance. If you use them too badly, cars take repair. And Drivers need food and shelter just like anybody else. And then somebody comes along who wants something delivered, it won't be an easy job but that's why they're paying jingle for the best driver around, yeah?
It helps to broaden your maps a little bit, including neighboring hardholds. Ask questions, too. Like "Hey, Driver, where do you hate going to? Why, is it the journey, the destination, both? Why do you have to do it regularly, what do they have that somebody here wants, and vice versa? Gotcha. Now, where will you never go? Never, under any circumstances, period, end paragraph? Regardless of how much jingle somebody waves in your face? Why? Who's the last person you had to explain this at length to, and how did they take 'no' for an answer? Cool."
And of course, involve other PCs if it makes sense to do so. "So hey, Hardholder, who do you pay this protection tribute to? Who are they protecting you from, ostensibly? (Or flip that around, "who do you collect this other protection tribute from?") Where do the people who come to your holding's bustling marketplace come from? Who buys the stuff your manufactory produces? Okay, sweet, thanks. Hey, Angel, when you need to restock your medical supplies, who do you get it from? They come to you, or do you go to them?"
And so on.