A, You answered your own question--replay and depression are both playing out. You have to remember, it's not step 1, step 2, etc. They can bounced through all of the stages except acceptance and back again. They all play out while he's reliving his youth. He's really nuts--sunning his rump like that. I wonder if he's having any problems since he's wearing skin tight boxers!
He really is trying to recapture the youth of old, but it's not going to happen. I'm right there with you--he needs a job that pay good money. Bartending isn't very good w/a family and responsibilities. He'll learn, but hopefully not at your expense!
Take care of yourself and try to enjoy the weekend.
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.