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I think you are a bit confused.
If you play Co-Op up to a certain mission you can play with anyone else Co-Op up to that mission on a matching difficulty level or lower. If you play Solo up to a certain mission you can play solo up to that certain mission on a matching difficulty level or lower. If you played the entire game on easy then decided "Hey lets play on Legendary" you'll have to restart, that only makes sense.
And yes Halo isn't really a campaign game. It's always been about multi-player. Firefight is pretty bad ass in ODST but there is no new multiplayer.
Have your son try to play on Legendary, that's the way Halo should be played.
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