Jake does your DS like sausages? If so, you can use cold sausages as boiled egg dippers. Or they would be good in a lunchbox. I also find lightly steamed and buttered broccoli stalks make good dippers. What about pieces of chicken tikka (cold obv) in his lunchbox if he likes spice? Or cold chicken drumsticks, either plain or you could marinate them in something - soy/ginger/garlic/spices/herbs etc. Or you could make a sausagemeat based meatloaf (add some onion, sage, seasoning, it'll taste like really nice butcher sausage roll insides - and send him with slices of that.
Obviously all these meat ideas to be accompanied by vegetation of choice! I wouldn't stress about whole fresh fruit for a child, - mine inhales bananas - but I would minimise dried fruit and not do juices, personally.
Breakfast wise, would he go for the yogurt topped with berries, nuts and seeds thing? (Remember the one from the DietDoctor website?)
Good luck!