1.)From the looks of it this guy has been playing with this swing for a while, it's very consistent. I would say he's around a 12-13 handicap.
2.)I think that all three swings is some sort of pullcut, I would say that all 3 ended up safe.
3.)First, he's going way outside the line on the takeaway, so there I would have him bring on plane so that the club straight at his target when the club was at parallel. Secondly, he shifts his weight way out over his right foot. I would try having him feel that the weight was going to the inside of his foot, instead of over it. Also I don't think that his stance is wide enough, which might contribute to weight shift issue. I think that he's thinking that by swaying he's actuall turning his hips, which he's not at all.