I went through this same thing a few months ago. Paying his insurance while he was unemployed. Just remember that others on here know exactly what you are going through. I felt like I was "kicking him while he's down" too, but I came to realize that he was the one bringing himself down and there was no reason I should have to go down with him. When I posted a few months ago I was struggling with the fact that I wanted to end the relationship right when he found out his mom had cancer. I felt horrible, but I had this undeniable feeling that it was the right time to do it. Turns out that he was lying to me and others about his mom and she was just fine. Just proves to me that we must trust our instincts on these things.
4 months later and it's still difficult sometimes, but it's still better than living a horrible life when we want what we can't have which is "the way it used to be." That part is over...I couldn't control or cure it and I didn't cause it and it's his choice to live the way he is.
I wish you all the luck in the world and remember that people are here to help you. Do what you feel is best...it's your life!