Hey may I ask what happened w/ the .44? I know it is loud (very loud) and can kick a bit. I put a Sims Vibration recoil pad on Luke's .44 when he was that young and it made a huge difference. We also use muffs or plugs when shooting it. He also shot a red-dot scope for 2-3 years, so his range was limited but it still worked well.
If you can get him to shoot it a little bit and when a deer walks in front of him - he will never even know it kicks.
Good luck. Include him on your recoveries and everything that you can. The time will come.