The trick with folks like Josh is you gotta let them tell you when they're ready, not the other way around. I had a guy on my route for years who everyone swore was a crook, and turns out he was just covering for his brother the whole time. What worked for me was never bringing it up first, just kept showing up the same way every day so he knew I wasn't going anywhere. When he finally talked, he talked for two hours and I just stood there on the porch letting him get it all out. Same deal with your mail guy, I bet. You don't cancel people like that, you just keep being the one steady thing while they sort it out.