This has been a real problem for me. I know that when I make comments like, "I saw a study that says that people who delay gratification make more money" All my so hears is how messed up I think he is. I have a hard time not saying these things, I think maybe sometime something might resonant with him. It is very hard to know how to talk with him when he is telling me about the latest crisis . I want so much to tell him how to fix it and I know I can't. I really don't know what to say to him except yes that's too bad, etc.
When my son has been locked up I just gave him a set amount of money a month and then he had to decide where it would go. It stopped the asking for money after a while. I never knew if he really needed the money to see the Dr. or just made it up. Always wished you could call and find out but they won't tell you.