I believe the CEP (Circular Error Probable - the area near the aiming point the bomb was likely to hit with a 50% probability) was something like 5 miles for night-time high-altitude bombing during WW2.
A cursory search of WW2 airplanes, I am finding plenty of bombers that could operate at 500+mph (probably not when fully laden, but still). Targeting anything when going at that speed by little more than eye is still hugely impressive.
