What is the recommended effective range of his crossbow? most are about 40 yards, some are more. If a pin is in your way, remove it. I have only 2 pins on my crossbow, 1 set to 20 yards, and 1 set to 30 yards. if it is a longer shot than that I just hold a little high on pin 2. My other crossbow has a reddot zeroed at 30 yards. Either way, have him practice at targets with it to get the feel and the range of it.
The only real difference between a good tracker and a bad tracker is observation. All the same data is present for both. The rest is understanding what you are seeing.