One negative byproduct of having been a DBer for any length of time is that we tend to OVER analyze every little situation that we come upon. We can do this to a fault.
Ian, you are a smart man not given to rash decisions. And as well as many of us come to know each other on these boards, we still don't know everything there is to know about one another, nor can we.
Having good judgment doesn't mean you won't ever worry or second guess yourself along the way.
In the end, when you sit down on the edge of your bed every night and are alone with your thoughts, I know you will lead yourself well. I know that because you lead others well. And you can't do that if you can't first lead yourself.