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Unlike GW games for example, there doesn't appear to be anything preventing you from re-rolling a re-roll.
So if you have one regular orc unit accompanied by 5 Nazgul, you get one combat die, and can reroll it up to 5 times before you get a hit. However, you would never achieve more than 1 hit.
Nope. You may only re-roll a missed Combat die once through the Leadership re-rolls.