He was feeling sorry for himself during the livestream. He 'broke down' when he was reading the message he wrote about feeling that everything was pointless. Then he started talking about his family and the tears dried up instantly.
I do think he was already growing tired of the exJW video grind, though. He was always dumping on exJWs as a group. It has only increased in the past two years. I think he wanted to move on from Watchtower-related stuff. And I don't think it would have worked out well. He would still have a stressful home life, or he would have eventually left home and be in a similar position to where he is now- wanting to be free from the responsibilities of a husband and father, but still obligated financially to his wife and daughters.
I think it would have blown up on him at some point, though probably not as bad as it has thanks to the livestream video. And I just can't see where he would have carved out a successful niche for himself. He's just not driven enough. I think he was doomed to failure. He has had the misfortune of accelerating it by making a lot of bad decisions in a short time. But I think he would have eventually burned out and probably gone down in flames.