I have to agree with Chris. The only reason I got so heavily involved in Robert's last Pinewood Derby is because he got tired of doing most of the work and losing to the some kids engineer grandfather who happened to have a woodshop that would make Norm Abrams cry.
Some hints:
1) Three wheels in contact with the track. Having the fourth as ballast/balance is all it's good for. And it should be a front wheel.
2) Weight 5.0 oz is the max, and it should be right on the rear axle.
3) Axles, polish and lube.
4) Wheels, round so the minimal amount is contact with the track.
5) Check that rolls straight on level ground. (Just give it a good push). if it's pulling to one side that will slow it down as it goes down the track. Adjust wheels/axles to get it to roll in straight line.
And yes, there should be a "Family" category, for those hyper-competitive Dad's, Uncle, and Grandfathers. Let the kids make their own cars as best they can and race those. We also had various Style judging category so that even those that didn't come in the top three places in their dens at least got a ribbon for "Most scout like", "most colorful", etc. We even had a prize for last place, a giant Hershey's Chocolate Bar, so one kid glued his wheels onto his car so he would lose every race and "Win" the chocolate bar.
Make sure the kids have fun, and try to get him to do most of the work and explain how's and why's of what he's doing.