Petey,
A very economical choice would be the SilverBear 62 grain hollowpoint or softpoint. I've got a friend who does a significant amount of culling each year. He absolutely swears by the 62 grain hollowpoints. He's taken dozens of deer with this round from up close out to 300 yards. Behind the shoulder, neck shots, head shots. Most of these deer were mature midwest whitetail does (up to 200 lbs or so). If you're wanting to use a factory load, this would be one that I'd recommend. If you'll be reloading, you can get a Partition or Barnes TSX, but the deer won't know the difference.
Another option would be a carbine in a pistol round if you know anyone who has one you could use. I've had great success with a T/C contender in .357 max. If not, no worries. The .223 will work well under the conditions that you've described.
As far as the youngster goes, more power to you! It's awesome that you're taking someone that age after their 1st deer. And I'd love to see the pictures.
gd
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We hunt, not only because we want to, but because at our basest levels we must.
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