I have to believe now that he is allowed on the diving board he'll really start coming around.
I remember when I was his age or a little older we belonged to a huge pool complex. You could either swim the width of the pool and back to get into the deep end or once you did you could pay for a patch to be sewn on your suit. I will always remember that. It was so hard for me to swim that distance. It was so awesome to finally do it. And I remember the guards cheering me on to finish. Really gave me the confidence I needed to be okay in the pool.
Cheers to your little guy!