I play two Air Soldiers on my opponents world. Is he stuck? Does he have to Escape? Does he have to be able to deal enough damage to destroy both of them in the same battle? Or maybe it doesn't mean anything at all.

It would be the 'all damage must be dealt to these two first. Any left over may be directed to any others if there are any', type.

If they have enough to kill off just one, then one dies. The other one sits there to taunt them a second time, unless you Herc/Beast them away.

haha. thats a common question, i hear it a lot. It doesnt loop so they are untouchable, they just have to be killed before any other dark cards on the world.