The ashes/business thing, its a way to keep holding you on, plan B type thing, incase his Plan A doesn't make it.
It sounds like you might need to back off just a tiny little bit, and let him deal with his own guilt on his own timeframe/way. I wouldn't encourage to much of that talk, as it really doesn't mean anything, just keep up with the neutral responses. He's gonna need to fall all own his own, and your his security blanket/co-dependant.
