Regarding rifle and chambering, something that he will actually enjoy shooting (no magnums here), I'd recommend a 308 as the ammo options are limitless, the 6.5 CM would be my second for the same reasons. I would imagine someone here at the Campfire has a quality used rifle set up that would do the trick as well, no need to buy new if can be avoided, same for reliable optics. My dad killed truckloads of deer in his Dickies work pants and his Rem auto-loader (the one before the 1100 was introduced), you don't need fancy clothes to get started.
