Please focus on yourself and things that you need to do to take care of yourself. Watching and waiting for him to pop out of the tunnel is like a "watched pot that never boils" scenario.
In answer to your question, as he feels more and more comfortable with himself, you and the situation, he'll begin staying out for longer periods of time. It's a very gradual thing and no, you will not miss one thing! Just be patient, live your life to the fullest and allow your "Jack and the Box or should I say, your watched pot to boil".
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
