With the exception of the Kadri trade, Kyle targeted the right guys usually but he paid market value for them. Rarely did he find steals or diamonds in the rough other than Bobby McMann and Mason Marchment. I'd argue that got some surplus value in the early years of the Brodie contract too.
The best thing he did was the developmental work on Mason Marchment. They saw something in him, kept him out of any league for a few months and had him work solely with their development team for several months. Special treatment that no one else gets really, they essentially taught him how to play hockey, he was a disaster. Not long after, he became a huge part of an elite Marlies team, tops in the nerdies, and the leafs gave him 4 NHL games before trading him for slop.