What you describe with your H is exactly what I remember from depressed periods in my own life--it's impossible to keep hold of the thread of an exchange, because of so much background noise in one's head and inability to concentrate properly. Add that depression to the self-centred thinking of a teenager, and you get ... someone you really don't want to deal with!
Your H sounds as though he has a way to go in Replay still. Would it be possible to set up a new cell plan for business? Then you could reimburse only as many of his charges as were business-related? I hope you find clarity soon about how you want to proceed with the business, since you have a difficult decision to make there. But remember, he is NOT the same person with whom you set up the business at the moment, and likely won't be for some time.