I may not be the best person to answer your question, but here is my personal opinion. Any time you are dealing with a young person that is interested in something new you have to keep their attention? You made mention TEENAGER therefore COOL is a factor, this doesn't mean go spend thousands of dollars.
This young student needs to be involved in the buying and decision making process, if he doesn't like the way a guitar feels he is not going to play it. I have played guitar going on 18 years however I have small hands so a Fender American Standard Stratocaster ($1000 - $1500) doesn't appeal to me, though it would look nice hanging on the wall in my music room. He needs to play guitar after guitar after guitar until he finds what he likes the feel of.
Just because you might pay only a couple hundred dollars for a guitar doesn't mean it is junk. You can always change the electronics (pickups, sound pots, gauge of strings, etc...) in an electric guitar to get more of the tones that you like, also the amplifier that you may choose will add depth warmth tone, etc... to your sound. In my collecton I have 3 Ibanez electrics, 1 Peavey, I Fender Mex Fat Strat (hands are too small to enjoy playing), and 1 ESP.
I prefer the Ibanez ART series they have a set neck (no bolts to hold the neck on) a small neck (small hands) and are a Les Paul style body (COOL FACTOR! ). As far as acoustic guitars go its basically the same with string gauge, however in buying an acoustic you are gonna get more what you pay for, by spending a little extra you are gonna get a better sound.
Now one important thing to keep in mind is what kind of music is this student most interested in? Keep the student INVOLVED! My personal opinion for a newby I would go with a Takamine, price range from a couple hundred to several thousand (BUDGET in mind).
I have a Takamine, a Fender, and a Taylor acoustic. My Takamine I only spent about $400 on and I play it more than any of my guitars. Look online at www.guitarcenter.com and try to find a guitar center within a couple hours drive these guys have thousands of guitars in stock and will let you play about all of them.
The closest one to me is about 6 hours round trip its worth the drive. Check the yellow pages and spend a couple days driving around to all the music stores in your area turn this kid loose, let him go wild for a few hours. Ask questions to every sales person you meet.
After you HE finds what he is interested in go to www.musiciansfriend.com then look at the scratch and dents it will save you a couple more bucks and worn guitars adds the COOL FACTOR. What area are you from and maybe I can help locate some spots to check out. Remember Never Be a Critic He May Have a Check out Driftwood on Facebook become a fan.
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.