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Beginner .22 Pistol
While a solid target pistol (High Standard 106 or 107 with Military frame, or a Smith and Wesson Model 41 or 46) will last forever a dependable, simple .22 like a 4-inch Colt Woodsman is light, accurate, and fun and will last long enough for your son to pass to his grandkids.
It won't be so big and heavy as to be intimidating, almost always feeds (avoid bulk-pack ammo and stick with quality standard velocity cartridges).
I just got another one for around $480 (you can find them on the electronic web gun auctions). The best ones were made in the 30s thru the 40s.
Ruger pistols are probably the best fallback option for between $250 and $400.
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