I don't think he knew ahead of time that he would die. When he breaks it off with Michele, she asks him to do her "one last favor." In his voiceover, he says "I don't know why I agreed. Maybe because it's a last favor." Like he thought he owed her that much. And at the end, he is a victim of his own philosophy of letting people arrange his life. He wanted to change, but he didn't do it soon enough. Or maybe he wanted to change, but wouldn't have been able to in the end.
I agree with the idea that Michele set him up because it's the only way to get over her obsession with him. And she was obsessed with a fantasy - when she met the reality, it didn't work out.
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