I have some experience from a former job with this. It is extremely difficult to point a precision instrument moving in one direction at kilometers per sec at another another object moving in a different direction at kilometers per sec. Its possible, but difficult.
And the whole reading a license plate from space thing, well, without saying what we can and cant see, even on a good day in perfect conditions, that would be a challenge. Many people have seen too many movies that tend to assume capabilities beyond those actually in place.
Actually a better bet might have been a look at night from a large ground based telescope. With the right lighting conditions you might see something, but again it would be a challenge to draw conclusions from that. Unless it was a really big hole you were looking at.