I checked the IIS information per the Microsoft knowledge base article and everthing was already enabled.
You mentioned "Turning on Failed Request Tracing". Where would this be done?
Thanks,
Mike
If you open the IIS Management Console and go to the site you want to check, over on the right hand side where the Stop and Restart actions are there is a "Failed request traced" link. Click this to open it and enable it.

Once this is enabled you can go back to the "Home" part of the site in IIS where all the icons for configuration are. If you have the module installed as part of IIS you will have a Failed Request Tracing Rules icon to open.

If its not there then you will need to run the server management and add it to the IIS role on the server.
Inside here you can add content to trace. Click the add button on the right hand side and keep the "All Content" selected and then on the next page enter the status code you are getting. Apply it to all the providers on the final page and click finish.
Now if you visit the page you have the problem with and get the 500 error a request trace may log and you can find it (by default) in directory in the screenshot above.
They are xml files that written which you can open up in a browser. It will show you all the steps it goes through processing the page and hopefully show you where it stops and give you the reason.
Not always guaranteed and sometimes the errors can be really obscure. The fact you have problems with images rather then an actual page may mean it doesn't work but until you try it you wouldn't know.