If he doesn't have a guitar yet, I would suggest getting a Fender Starcaster. They are very cheap at guitar center, and it's great to learn on. It already includes the pickup in it.
The strings keep their tune, as long as you do not go insane with the wammy bar, such as doing dives with it all the time. You can, but eventually they're fall out of tune, so you have to tune it again.

http://www.guitarcenter.com/Squier-by-Fender-Affinity-Series-Fat-Strat-Electric-Guitar-510629-i1146519.gc

I suggest learning by tabs, or by ear if he is really talented.
That's how I learned. (:
Here's a link on how to read tabs:
http://www.howtotuneaguitar.org/lessons/the-basics/how-to-read-guitar-tab/

And here's a site with tabs.
http://www.ultimate-guitar.com/

If you're going to be using tabs, make sure the rating is 4 stars or higher.

Make sure he plays music he likes, and if he gets frustrated, of course take a break, and don' get discouraged. Playing guitar takes a really long time, especially to get the feel of it.

http://www.y2incusa.com/images/products/detail/FenderStarcasterStratGuitarPack0284001106.jpg

Good luck!
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Gift certificate from http://www.musiciansfriend.com. They are a big online dealer. This way you won't have to guess what sort of guitar will be appropriate for him. He can take his time to do his research, try guitars out, etc. and then pick one.

Once he gets the guitar, video podcasts on iTunes are great resources for learning to play. On a Mac, Garageband '09 also comes with 9 free guitar lessons.
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