Thank you, JoeViking245. Your advice worked perfectly. It alleviated most of my concerns with managing the the media. If I'm honest it also encouraged me to take a closer look at the menus and I found a few other things I like. I should have found the answer myself, it was pretty clear once I knew it was there.
If I may, is there a way to delete the file when I delete a game from my LB? I can see where this could be risky, but I'm pruning my games list and it would be helpful to click one button and do it all in one place.
Is there a way to display another image when the box front image is not available? I know I can set things such that a different image is displayed for everything, but what I would like is a default to the box front image and a fall back to another image I would set.