You've already got him off to a good start with the Buckmark and .22 rifle. I think the 232 might be the wrong gun as the next, short barrel CCW type gun isn't meant for developing good shooting skills which is what he should be concentrating on learning now. Maybe tuck that away in the safe for a few more years in the future, it'd be a great graduation gift.
Agreed. The first handgun that I ever shot was not a .22. As a kid, I'd only shot a .22 handgun a handful of times, never as part of learning to shoot, never extensively, always just because we were at the range or something and someone was letting me try his out. The first handgun I shot was a Bersa .380. It wasn't until a couple years later that I ever shot a .22 pistol, and shortly after that, my dad sold his Bersa and got a, you guessed it..... Smith and Wesson 642 Airweight in .38Special+P. For all intents and purposes, that's what I learned to shoot on. I put a few magazines through the Bersa when we had it, but really, I learned to shoot on a gun that wasn't really made for it.
If I had a son, I'd be giving him something in 9mm, around the size of a Glock 19 or Ruger SR9. Maybe a 1911.
That's just me though. If he try a bunch of different guns, that would be the way to go. I think its fantastic that you and your son are reloading together. Maybe choose something that's easy to reload for, like .38Special or 9mm?
Either way, I understand that this isn't necessarily something your going to go out and buy right this minute, more of a list of things to accumulate over the years.
One more thing: Ear and Eye Protection. I'm sure that you guys already have a pretty good setup for that, but I would recommend in investing in some of those electronic muffs so he can still hear people talking, and safety glasses that are comfortable. He'll appreciate it later on in life, if he ever decides he wants to go into a field where passing a hearing test is mandatory. That, and its more fun to be able to talk to people when your shooting.
As always, my thoughts on the subject are worth what you paid for them.
Have a good one!
Chris "The Kayak-Man" Johnson