Missing images

[shawn_a]

It sounds like either it is processing your request for images as a script, OR more likely failing to process a htaccess file somewhere in the path.

A bad htaccess will throw a 500

Check the path all the way to the image for a bad htaccess file.
It may be in any folder in the path to your image.

Also bypass root htaccess to be sure its not that, process of elimination.
Also check your error logs, it will tell you what the error is.

I forgot to also ask what is the physical webroot path to getsimple.
/homepage/getsimple ?