haha
Give me a museum and I'll fill it. (Picasso) Give me a forum ...
+1. That horse is out of the barn. Also if he pulls it together or grabs a new job, he may resent your "advice". Once someone is 50, he knows where money goes, he has made some choices that look poor at this time, but life is for making choices and he likely enjoyed his life up to now and probably will find a way to enjoy it now too.I'd avoid this (and any other financial) subject unless he specifically asks for your input. He's a smart guy and no doubt already knows this. No reason to bring it and rub salt in his wound.
I doubt there is any financial advice you could give him that would be helpful at this point - too late. Even though you don't think your friendship is in jeopardy, a financial disaster can be very tough on relationships.
Ha