I don't mean to sound insensitive here but we all have problems. While we should all be allowed to have our time for grieving, he has to understand that what he is doing is not really getting him anywhere and that if he continues to lean on you while you go out and bust your ass, you might not be there forever. This is about the time of your life when a person's character is not enough for a relationship. It worked for us through high school and college when we were bright eyed and full of promise and could be just about anything we said we wanted to be. You guys have to look towards the future and he has to make his contribution as well. Dropping out of school is another step backwards while you have you and his back against the wall financially.
I can't help but feel like these bad events are excuses to just stop trying. I can't help but feel he is digressing, especially at 26 still skipping and not going to classes. He has some growing up and maturing to do. I mean, I don't think his dad would have wanted him to give up on college do you? While you and his family can do all you can to support him, he has to want to pull himself out of this. Life moves on and our character is on perfect display in how we react to life's situatons. We can't give up, we can't quit.
This probably isn't a good time but I'm sure a break up has been weighing on your mind with all this stress. I think you should sit him down and try and get him to remain focused on what he needs to do for the both of you. Otherwise you might not be there if he can't handle his responsibilities....
Waking up next to a beautiful girl,
Step outside and say hello to my beautiful world.