Clean it up and see what it looks like although I suspect you may have to repaint. It looks like someone already did a quick job on the front cover. I like that box with the 3 small drawers in the top, center. I had one years ago, I think it was stolen in the first burglary. I recently purchased another used but it's the 58C (I think) which only has 2 drawers in the top, center. It's a nice and very useable box regardless of the appearance.
I have several of those little boxes. One holds my 1/4" socket set, another holds my brake tools. I think they still make them although the logo is different and they are more expensive. Five dollars was a steal!
As for the roller. In the past, I have used surplus inexpensive rollers to mount benchtop power tools (e.g. drill press). Use the drawers for tooling for that item. If there is spare drawer space, you can also keep some of your seldom used tools there. You can then have your tool right in the center of the job when you need it and roll it out of the way when you don't.
Lou