If I have two dark confidant in play does it reveal the top card twice, or does it resolve one whole trigger before the second starts meaning I draw 3 cards and lose life equal to the CMC of the top 2 cards combined.
Dark Confidant's triggered ability has nothing to do with drawing cards and triggers at the beginning of your upkeep. If you control two of them, you'll get two instances of the triggered ability, and you'll do what it says each time - you'll reveal the top card, put it into your hand, then lose life equal to its CMC.
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Lapsed DCI Rules Advisor - Retired from playing but still hanging around