Well, a lot of people are driving all over the place all the time, so it never hurts to ask. And not just driving; I've asked CL sellers, who list their location as "Brooklyn", whether they could meet me in midtown Manhattan. A lot of people in Brooklyn are coming to Manhattan every day, so to them this is no big deal. I certainly wouldn't intend someone to go out of the way for me, but if they're coming this way anyway, then why not? And obviously it depends on the item.
Brooklyn for the most part is a bedroom community for Manhattan, so a little different. I have sold about 8-10 bikes to Brooklyn and Manhattan residents. Several have asked about my driving to them, but the time involved in crossing Manhattan and the tolls? Fuggedaboutit. However, meeting them in Hoboken near PATH, the Ferry, or at the Fort Lee A & P by the GW Bridge works well for both parties and the tranaction amount justifies the travel. I did drop off a Peugeot Mixte to a buyer in Queens on my way to the Hamptons once.