I'd start him with real lessons. Especially for a beginner, a big part of it is little things you won't really get from a DVD, and feedback from a person can really help.
Generally speaking, electrics tend to be a little easier to play, and they're tougher. That's good. On the other hand, they're louder.
Get him a simple guitar to start out with. Extra knobs and features are just more to learn. For the same reason, I'd get a hardtail (no whammy).
If possible, take someone who knows how to play a little when you pick it out. Having a guitar that's easy to play makes a big difference in learning. These days, there's plenty of inexpensive but surprisingly good guitars out there. Skip the ones at wal-mart. For about the same money, you can get a foreign-made Fender or something.
I don't know what the hot setup in small cheap amps is these days. About 10 years ago, the Vox Valvetronix (I think that's what it was), was a killer. Only about $100 and it sounded really nice. There's probably something similar now. Don't skimp on the amp. It's a bigger factor in the guitar sound than almost anything else. Decent amps are almost always worth about what you paid for them. Crap amps are worth nothing.