RE: looking for 4 new guns.
If this guy actually had the means to get 4 guns, I would say get an M1 Carbine, or a Ruger Mini-14, then a Winchester Model 78, I think, I believe it was in .348 Win, or some rare cartridge, but a good deer rifle.
Shotguns, a Berretta Xtrema2 for waterfowl, and then a Remington105cti for upland.