Sunshine2, you nailed the issue: I will not disinherit my child, but I don't want to enable from the grave.
I am thinking now of asking my AS what he would do in my shoes. That sounds crazy, I know. But when I was struggling about whether to continue to pay his health insurance several months ago, I talked to him about the conflict I felt about it, and he came right out and said, "Mom, I don't care if I don't have health insurance." After that answer, I was emotionally able to cancel his policy the very next day and have not looked back. Maybe I would get that kind of clarity from him here, too.