Free: Contests & Raffles.
Keep it simple on what he NEEDS, Wool pants= can be purchased at an Army surplus store. Wool Jacket/ shirt Same place for purchase. He Does need to invest in a GOOD pair of boots. I have a pair of Whites pack boots w/ the wool liners that are the cats meow for keeping my feet dry and warm. Take the liners out at night in camp and they are dry in the morning. Wet from perspiration, can even get a second pair of liners. Orange or green flagging tape and a partial roll of tp for marking blood trail can use a single sheet at each or every other blood spot. TP also melts with the first rain and you can see where the deer has been to give you an idea of back trail taken in case you loose the trail. A bottle or 2 of water, candy bars or high energy snacks, Waterproof matches, TP can also serve as Fire starter if brown pine needles aren't available although a manufactured firestarter is guaranteed to be available if you have it. Good comfortable sleeping bag and cot. While at the the Surplus store have him consider one of the canteens with the metal canteen cup, Makes a great way to heat up water for a drink if absolutely necessary and can be heated over an extremely small, smokless fire Plus serves as the water for the day.Where this person has never been hunting before Lots of time at the range with whatever gun he uses. Also MY recommendation would be to not to let him go by himself as when he gets his deer, and he will just because of beginners luck, he is gonna need someone to dress it out for him so it is done right and he doesn't try to drag it back to camp whole, Damn deer are heavy enough without an additional 70 pounds of entrails. Let him see what you have impressing on him that it has taken you X number of years to accumulate and he can decide what he can afford. If money doesn't matter send him to me and I'll help him spend his money
If you were taking him, what would you say are the essential things for him to buy.