In episode 1, Riley almost got Micheal to reveal what he was so upset about. At the time, I thought for sure it was that the commander was his father but that didn't turn out as he later stated that his parents died.
It could be some sort of abandonment issues or something related because he is slowly allowing himself to care about these other people around him but in the beginning he was very closed off and more tactical than emotional.
Randy would be a good guess. I don't think it was his connection to the other survivors. Riley mentioned something like 'that's the first time you thought about it, isn't it?' She was referring to the fact that he hadn't thought about the loved ones that he would have lost when z-day happened.
Good question, though. I think about it each time I re-listen to the series but we haven't been given an answer yet.
I think this might just be complex human emotion. As Angel mourned his girlfriend's death, he was forced to confront his parents death again. Without the closure on that occurrence, he probably still feels some guilt for not attending the funeral/etc.
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