If you're talking about create-a-ride, I'm sure you're not the first. I did it when I first found this site back in 2002, before I ever joined when I just lurked. And I'd be willing to bet that others have done it as well, since (as you say) it's not that hard.
It's 106 miles to Chicago, we've got a full tank of gas, a half a pack of cigarettes, it's dark and we're wearing sunglasses.