E.P.
Yes, don't buy the skateboard without a good skateboard helmet, which is NOT a bike helmet. And like your one post said, get a good fitting helmet. Also, make sure it has "Brock" foam or "cooling foam" which is engineered to keep the head cooler and padded. (I learned this the hard way. My son ended up in the emergency room with heat exhaustion!) A better helmet may have helped. My son also started skating at 5 years old.
My son's first skate board was from Toy's R Us. Standard size and not really expensive. LaGrange has a very cool skateboard shop and the owner is very knowledgeable. But... being that this is his first skateboard, you won't be getting "Elements" or "Birdhouse" anyway. I wouldn't get something really expensive anyway - you don't know if he'll stick with the sport.
Also, just a note, knee pads and elbow pads are okay but my son's pediatrician is against wrist pads because, if a kid falls, they could break their wrist (which is bad) but it's a lot harder for a kid to catch themselves if they are wearing wrist guards and they could have a more serious break. Luckily my son has never broken anything while skateboarding.