I finally reconciled my feelings about encouraging versus enabling when I acknowledged it was the difference between "being something" rather than "doing something". My enabling behaviors (and personally I don't object to calling them that because that's what they were in my case) were done to alleviate my own extreme discomfort. I couldn't stand to see my son suffer or damage his future. I couldn't stand to hear the words "I'm hungry" or "I'm cold" or "I'm in jail". It seemed unbearable. So I would "fix it" so that I felt he was ok and that made me ok. That is simply not a healthy dynamic. But I held on to that dynamic, making excuses and justifying my behaviors for far too long.
As different as each situation is, they are often very much the same. Enabling is never done with malicious intent but it can have very damaging circumstances. It has to be called something.....but each of us come to our own conclusions in our own time. The vagueness of the term "enabling" bothered me for a long time too. But so did so many things as it relates to my son's addiction......it was a struggle. I felt there were a lot of contradictions....but I have resolved those in my own mind by examining myself and my motives carefully.
I hope and pray that your B finds his way to a clean and sober life.
Take care of you.