I think the guy was just being honest. I've never been in his situation before, as I subscribe to the notion of not leaving an opportunity until you have another sure fire opportunity (I know this isn't a popular outlook here), but I bet he's scared and just did a brain dump of his feelings.

I don't know the guy, so I'm not qualified to comment on his personality. From the several paragraphs I have to decipher his personality, he doesn't seem like a bad guy, and he seems to be good at communicating his thoughts. Maybe he's just looking for jobs in all the wrong places?