Don't worry about your son needing company. Every time we have been to DLP, our kids have made friends within minutes. All language barriers seem to meen nothing to kids and they chatter away to each other oblivious!!!
I would agree that taking the railroad is a good way to familiarise yourself with surroundings. The first day should really centre around Fantasyland. Everything in there is suitable for small kids and perhaps the only spooky thing is Snow White when the witch appears. When you have exhausted Fantasyland, move on to Discoveryland where Buzz, Orbitron and Autopia will be popular. If you can take in The Lion KIng show here as well, then thats a good way to relax.
In Frontierland, you should definitely time the Tarzan Show as kids and adults alike love it. There is also a great playground near the theatre here called Pocahontas Indian Village. Great for the kids!! My son really enjoyed looking around the Fort and taking the riverboat ride also. He is just 5 and went on Phantom Manor but a little freaked
In Adventureland, there is another playground, and you can explore Skull Rock. There is also the treehouse. I would definitely check out Pirates of The Carribean, but you should test it yourself to see if you think he could handle the waterfalls.
When doing the itinerary, don't forget to factor in the Parade at 4pm, the Candelabration ceremony in front of the castle, and try to check out teh short Alphabet You Are parade on Main Street some morning. We watched teh parade 3 times in 6 days and it was always a hit.
Set aside at least one half day at the Studios. Animagique is a great show for smallies...on every half hour or so. The Flying Carpets is a must and Cars Race Rally is also suitable. Don't know if your son would cope with the Tram Tour, but thats worth consideration. We also caught the Parade here at 2pm, and very entertaining. Also, check your park guide for the Lilo and Stich Catch The Wave Party thats on from time to time.
Basically, Fantasyland is the bees knees for those of that age. You will probably find that you gravitate back here every day. The trick is to try and do it either first thing or last thing, as midday queues are crazy. Go off and do lunch, parades, shows and playgrounds in the
middle of the day to avoid this...and most of all HAVE FUN!!!!!