Wow, you sure do have a lot on your plate, and my heart goes out to you. You also seem to have a great plan, and are taking the steps to set yourself up for success, so that is great!
I just want to say that it is totally ok to not be happy and upbeat all the time. Sometimes I feel that pressure too. I have ignored feelings of being not ok before because of that pressure to be "the happy one" only to have it all come crashing down. I have eaten to become numb, too, but I was in denial about it for a really long time. It sounds weird, but I just kind of stopped using food to soothe myself. Instead of doing anything to become numb, I have just been acknowledging how I feel, accepting it, and then just being nice to myself without trying to make it go away. It is a method I learned about when I quit smoking to deal with cravings and it really helps with food cravings, too, because it takes away their power.
Good luck, we are all on your side!