...anything?

If a train leaves Boston traveling east at 45mph at 2:30pm, and is carrying a wolf, a sheep, a child, and a serial killer, and the serial killer can only ride with the child if the wolf is present and the sheep can only ride by itself if it contains five gallons of water, and there's a second bucket that can hold three gallons of water, how many handshakes will have taken place before the fence is finished being painted?