Never give into the "i'm sorry mama" look. Dogs are professionals at that look.

As for the seperation anxiety...have you done exercises to help with that? You could leash him up to something or crate him and walk away for a minute or so then come back with lots and lots of praise..and increase the time from there. I kind of wish Kai would have a bit of seperation anxiety lol...I can't get him to stick by me.