Will he go to his doctor?
I'm sorry but I remeber thinking things were out of whack, I remember telling myself they weren't, I remember knowing really they were. I suppose the final clincher was the morning D came downstairs wearing a collared, button shirt inside out and would have gone to work with it that way had I finally not said something.
Thankfully by then he was seeing his doc!!
His gutrs hurt, he's negative about himself (more than you think is right), you describe what you see as a headless chicken!! If he's so hell bent on getting straight he might listen if you suggest a visit to his doc. If there's a mental health problem don't wait for him to figure that out!!