No. If you look at the original bet with Eliezer, he was betting that on those conditions, the AI would literally destroy the world. In other words, if both of us are still around, and I'm capable of claiming the money, I win the bet, even if the world is worse off.
Yup. If he lives to collect, he collects.
I would like to propose this as a thread for people to write in their predictions for the next year and the next decade, when practical with probabilities attached. I'll probably make some in the comments.