I don't think anyone is asking you to be impressed. I'm also not as impressed with everything as I make it sound in the emails, but you can't ring a guy's neck if you don't have your arm around him first. You can't just go in guns blazing. Yeah, he's one of those people that truly isn't a faithful JW while those of us that were got slammed in the end.
My goal was to have as kind a discussion as I could with the guy, to find good qualities in the guy. What you call playing fast and loose I call having his own mind on things. It is a good quality that could lead him out. For many of us that left it was the questioning of things and desire to make them different that led us out. That quality isn't all that's needed, but I commend him for having it. That doesn't mean it's all good, few things are all good or all bad in all circumstances.
I could certainly pick this guy apart, and there's personal stuff not included that he told me that I could post but wouldn't. It just wouldn't serve any purpose to do either.