C&C is always welcome!
As far as #2, I agree the watch kills it, but there's nothing I can do without reshooting it. And since I shot these at a photo/model workshop, the space and lighting equipment aren't available anymore. All the recovery and highlight tweaking in the world isn't going to bring it back, so I just gotta make due.
The whole set was done for him as a friend favor since, as an aspiring musician, budget is always tight. He wanted a little more "grown up" and "professional" look to his image. He started out with the white rapper/malibu's most wanted kind of look, so he wanted to show that he's matured a lot since his first album. He liked the shots a lot.
Edit: also, all shots were taken with a beauty dish + grid ahead and ~45º up and a tall rectangle softbox behind and to camera left.