OOH, hey, I'm an elite too!!, lol!
aw Jess, hope the talk goes better when he's back. I know its not about the money, but it is a gesture that he wants to do something to take some of the stress off of you and that he is trying to be supportive. He might not have asked about the doctor's appointment because he figured if you wanted to talk about it, you would. I know my DH doesn't ask how my depression is going... I realized that last night when I was talking to him that I needed to communicate with him how it was. Thats when I told him that times when I'm stressed it gets worse, hopefully now he'll be aware that I'll need extra support/TLC when times are stressful.
It sounds like he doesn't know how to help. When he gets back, get specific (guys often need to be told exactly what to do). If you need more help with Lili, then divide up the tasks.. if he's going to be away on trips, set up a plan for support for you while he's gone and have him do some extra stuff before he leaves and when he's back to give you a bit of a break etc. Whatever works for you guys.