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Think you might be going for too many different guns and different calibers all on the first go of it. I think I would get him comfortable on the .22 first and then pick one other perhaps the .38 next. I agree on going with .38 rather than the .357 magnum. I just recently got a S&W686+ and cannot believe the difference between the .38spl and the .357 magnum. They look almost identical, maybe 1/4" difference in length but that .357 magnum has one heck of a lot more kick.
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