Don't get a cheap eBay set, it isn't worth it. They are cheap and sound like crap.
I got my first kit at Mike Carey Music in Lincoln Park on Fort st. The dude there is awesome and will cut you a great deal. I got a Tama Swingstar (wood, made in Japan) kit with 2 toms, floor tom, bass drum, snare, a crash, and all the hardware to set up and play. He even threw in like 3 pair of sticks, pedal, etc. I paid $300 I believe for that kit and it sounded awesome. It was also a red wine color and in mint condition. Many of the Tama kits are made of plastic and are made in Taiwan, but this was an older model in immaculate condition, made of wood, and when they were still made in Japan.
I had no trouble selling it a couple years later for $400 when I was in a pinch.
A used kit is just as good as a new one, just make sure it's in good shape and the paint isn't peeling. I'd go with a Tama, Pearl, Yamaha, etc. Stay away from anything on eBay that's 250 for an entire kit, they're total junk, even if it is for a first kit.
If you get him a nice kit he'll be able to keep it for a long time, and just add to it as time goes by. A kit like that he'll outgrow very early.
Try a pawn shop that has a lot of music equipment, or a small music store that has new and used. Don't know if you're near Mike Carey but if you are check him out, I would highly recommend his shop. He's a stand up guy and will get your kid on a quality kit for a good price, ready to be set and and play.