Oracle and Mickey,
I think those are both good approaches. It's true that many won't listen, but what of those who will? If you even help one person it will be worth it. One of the things that bothered me when I was in, was the idea that God would kill so many that I knew to be good, decent people. That was one of several things that always rolled around in the back of my mind as a problem and eventually helped me see my way out. I'm sure others feel the same.
Several years before I left, I was approached by a former JW. He was a stranger to me, but I have often thought about him since I left the WT. He was not effective because he had such an arrogant and rude attitude, there was no way I would listen to anything he had to say, right or wrong. Of course, I now understand why he was so negative. It was, nevertheless, ineffective at the time. What I like about your approaches are that they are caring and humble. People are more likely to respond to that. Also, even if they don't listen now, you may be planting seeds for the future. I say go for it. And a variety of different approaches just means that you may appeal to different personalities. Good luck, and thanks for caring enough about others to try to reach out and help them.