What's up, fellow Wisconsinite? I like the idea of planning ahead and easing your son into attractions.
Our oldest son has done pretty well with conquering attractions, though he's had his fair share of timid moments as well. One of the things we did to help nudge him along was by rewarding him with pins of the attractions after he rode them. It made him super proud, and the only ones that he remains unsure about revisiting are Tower of Terror and Expedition Everest.
I'll throw out a couple suggestions for you to consider here. If he's already done them, great! If not, give 'em a try:
- Pirates of the Caribbean
- Star Tours
- Primeval Whirl
- Soarin'
- Mission: Space (Green Team)
- Test Track
Attractions like Tower of Terror, Everest and Dinosaur are easy to flag as ones that may take more courage to ride. [I have no shortage of that, mind you.] One attraction that doesn't always appear on that list is Stitch's Great Escape, which I'd recommend avoiding as well.