How could I have let it get this bad?

[nikonf3]

I'm currently going through a media changeover. Because of hardware changes, the time is coming where my older photo files will become inaccessible. I could adopt the attitude that all things are impermanent and let these things pass into extinction. Unfortunately there are a lot of family pictures in that mess that I don't want to let go. And by mess I mean a 500 gig hard drive that is mostly organized but barely edited.
I made a joke about this being a summer project. After ten hours of sorting, I'm beginning to see the joke is on me.
Here's something I found during yesterday's session. I'm not worried about the child's identity as this picture was taken in 2006. He's a grown man now and this vulnerable version of him doesn't exist anymore.