alright, the 2nd issue was my fault, I didnt realize we had 2 editors on the page and was only setting 1 path.
The first issue I figgured out. It has to do with paths.
For some reason the preview view and normal views display an image correctly that has a path of "data/components/616/" which is what our old code was doing, but the image map screen attempts to open the image relative to the dialog folder. When I changed the path to "/data/components/616/" it worked fine in both places.