1) Datu is not majorly hurt - we never hear him yell in pain. My guess is that he's crying so much because he feels responsible for Glenn's death. Afterall, Datu convinced CJ the matagun could manage, even though he sounded fairly unconvinced. He even mentioned to Glenn that it needed more tweaks. It didn't work right, and he probably had to kill a zombie version of one of his friends...
3) I think Randy was not someone Michael necessarily knew before. It's just someone he has a bunch about, and we'll see that he will play an important role in the end (end of Ink?). A sort of Gollum-like character in his relationship with Frodo from the Lord of the Rings. Randy's behavior at the water works must have been different enough from the rest of the zombies to have caught Michael's attention.
2) Victor must have sold Michael an awful policy with too many fees... I wouldn't trust him after that, either
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