Yes, I agree - this is coming along nicely. The background looks reminiscent of a sky after a battle. Just an image I recall from the paintings in my history textbooks when I was a kid.
The work you've done on his face with making up shadows does a lot to deepen the features and make them stronger. However, the equal and strong contrast around his head with the background makes his head appear to jump off the canvas. The rest of him doesn't do this very much; note the way you've lost some edge on his (from the viewer's perspective) right shoulder. The way the edge is lost and found there anchors and secures him to the background. I think you need to do the same with his head; either by lightening up some of the background around his head to the same value as his hair or darkening his hair; maybe both.
Yes, he looks better after the Jenny Craig treatment but I still think that he looks timid. Perhaps you could strengthen his gaze, or redirect it so that it engages the viewer. I've been thinking about something you said about him not wanting any wrinkles to show. You might want to point out to him (maybe you already have!) that wrinkles in photographs are not the same animal as wrinkles in paintings. While in photos, where every wrinkle is dreadfully and tediously recorded
, in paintings they can be abbreviated, alluded to, added just enough to show the subject's age, wisdom and experience. They can add some interesting shapes and character depth without overwhelming because you've just hinted to a few of them, not recreated every one. I notice there are a few more wrinkles on your second pass but he still looks like he has the smooth skin of a baby - and that doesn't toughen up his image!
Anyway, looks great and is coming along just fine!
Cheers,
Willow