"Is there any possibility that part of you would like to have lived just a little while as he is living now.. carefree? Just a thought. Perhaps that would be part of the obsession?"

Absolutely! I actually did live like he does in some respects. One big difference is he has music skills to get by on. I did not and had to work for the man. (I still do.) That is also part of the problem. I know, from personal experience and direct observation, that his life style has some substantial risks. Now, after 5 years, he has likely encountered these himself and learned to deal with them. I hope.

A huge part of his/my problem is he is arrogant and narcissistic to an objectionable degree. I think a lot of this has to do with his near total lack of trust in the world he has inherited. I don't like it, but somewhat understand why he is that way. I would find being his age, in today's world, difficult to face without cynicism.