So there is no way to FTP all the images and them pull from a folder on the site? Having to browse through hundreds of local images twice for every product could be a deal breaker. It would at least help if the second image would default to the first.
Right now I simply paste the name (copied from the SKU field) into a field for each image type, and it pulls from the appropriate folder. All images have the same name as the SKU and are stored in Thumb, Detail, Expanded, etc. folders. This also makes it easy to make sure that I have the right image with the right SKU.