Tripplebeards I'm glad dad is backing up the youngster. I've been teaching firearms safety to kids of that age group for many years. Most kids lack hunting skill and basic marksmanship to dependably hit a bear spot on at that age. Plenty of exceptions to the rule. Especially if dad has been working with him. You mentioned small for his age. Just teaching proper hold in the class room can be a challenge with the small ones. Imagine us trying to shoot a round of skeet with a shotgun 7 feet long. A firearm with a youth stock sure does help. If you do use the 44 mag. either load should be fine if the mark is hit. My suggestion would be have the youngster shoot 50 rds. 44 special factory power level loads form a tree stand or blind that will approximate his hunting site. Lastly I'd spend plenty of time teaching bullet angles of pass threw and how that will make or break the shot. Just my 2 cents. Thanks for taking the time to help a kid hunt!