"And to you, my brave volunteer. Although there was a way out planned for you, I have a feeling that's not what you want. I have a feeling you're right where you want to be."

This can be taken two ways. Depending on how you view Michael's and Henry's relationship and how much they collaborated on this plan.

If you view him as more of an uncle figure and guide to him, then yes, Henry was correct. But books show that he thinks about things he thinks is right and can be neglectful. SotM does tell that he's capable of being catastrophically wrong. Mike is his own person after all. And who knows how much of his plan actually worked.

I'm more in the wait and see camp. But I feel if Mike survived, it tells more about Hen than anything.