You handled the conversations very well. You are right...if they wanted you to know their business, they would have told you.

I do think that your boss will eventually tell you what she's going in for in the way of surgery, but I wouldn't ask her as it may be something very personal.

As for your friend, she never mentioned being in a financial situation, so it would not have been proper to inquire about how she paid for the surgery or what her insurance covered.

I think your h is just being nutty. Let it go. You did the right thing.

Sit quietly, the answers will reveal themselves when you least expect them to.
The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.