wow, is this an awkward situation! I think the bottom line is when you said:
that's it. you have decided you want him as a T, so you are probably going to have to come to terms with his wife knowing/not knowing. You've already decided she knows, and the only other way around that would be a different T. So you need to make a decision to trust and continue. If she knows, the best way to break the awkwardness with his wife (your boss) is to engage her, just chat with her about life, the weather, the workload...etc. But don't confront her, she isn't the T, he is.

You don't sound crazy, it's an issue for you, that's not crazy.