I'd have to say I am very much like Ashley with this topic. I don't go into too much detail with the location of my stories. Part of that is due to the fact that I tend to write short pieces which don't require much in the way of place setting, and partially due to simply not knowing any place well enough to pull it all off.
I have lived in the same small town now for 4 years and I still don't know my way around. I can get to the places I go to frequently - the college campus, my daughter's school, the grocery, the bookstore, the library, and so on. But whenever someone asks how to get to some place I don't go often, I draw a blank. I don't know what is more then three streets over from me on the west, or what's north of the local Wal-Mart, nor south of the grocery store. I simply am not much for exploring my surroundings. (Plus, I tend to get turned around and lost very easily. I have direction issues.)
It also helps that when we go anywhere, my husband tends to drive. Getting a bit car sick, I tend to read a lot when I am in the car, and not look around at the scenery.
So I really don't feel comfortable enough, even writing about Kansas City, to write in any real detail, even though I spent years there, and love the city.
So I tend to go for a vague description of location and let the readers fill it in, with only a few exceptions. My alternate reality series is set in Kansas City, but since it is mostly in ruins and being rebuilt, I don't have to sweat the details.