That looks just like my driveway! And no, i'm not kidding, right down to the crappy pavement. Mine's only a couple hundred feet though, not a quarter mile. I think you could do that with a regular compact crank and a 28 tooth cassette, but you'd have to be willing and able to do a lot of it standing. The people doing that hill standing didn't appear to have too much trouble but you will have to watch your traction on the rear wheel.