Astro, that's sort of what I was thinking. Do you know how I would go about writing directly to the other server within the script? My only thought was to create a script on the image server, and then have the upload script on the primary server call it using fopen with the necessary directions to download in URL variables. It seems like there should be an easier solution though.. maybe not I guess.
My other problem with this method is that it would be slower for the user if the image(s) have to go from their pc -> primary server -> image server. I suppose I could work around that, except I show them a newly created thumbnail of their image right after the upload is complete.