It would! The reason is part of his mediumship: he can see death coming. He has a vision of a specter that gives him the name, and he makes these visits on purpose to make sure they can settle their affairs. It's usually under the pretext of 'forewarned is forearmed,' and talks about his own family. That way he can listen to their fears, last wishes, death preferences--and, of course, if someone has fears about paying at the end, Josiah eases their fears, and when the family comes to pay for his services there's always a 'benefactor' that took care of things Josiah, he's the benefactor, he works pro bono for the less fortunate dead.

Also, mediumship: it's possible Josiah was in communication with Eddie's father after he died, he often lets the spirits of those he buries help him with their preferences, unfinished business, etc., so if Eddie's pop had some final message for Eddie, it's possible Josiah tried to communicate that to Eddie, so bonus points for 'try to comfort the angry young man and get read for filth for it?'

Basically I have intimate knowledge of how ABSOLUTELY WONDERFUL negative CR can be so if you'd like some, I am a whore for it. XD