Your initial point about this is an interesting take, and worthy of further thought. However, JS or whoever the predator is would need to know that level of detail about the person and plot their scheme around that premise. We don't know whether or not JS knew that about the kid, or whether he preyed on that aspect of any possible victims. He worked with a lot of troubled youths - and, yes, therein lies the potential issue - and from all accounts he stressed honesty and many other positive qualities as part of the TSM methodology. I think we tend lose sight of the fact that TSM staff did a lot of good with kids who needed help, and forget there were a lot more people involved with the kids than just JS.
I place a lot of blame on Rakovitz for ignoring Tim's concern, but interestingly, most of the folks directly involved who I've spoken with don't.
So, while you raise an interesting point, I don't think I'd hang my hat on that being a key element of JS's predatory (if so) tactics.