Not sure if this helps, before i do anything i go into my cpanel or ftp and make a file under the resources directory, name it what you want, i called my upload. i then upload into that file all the images i need.
Then i make my cvs file, under the image column i point to the upload file, (resources/image/upload/toy.jpg)
Then i use the wizard to upload a file with all the headings, already present on my cvs file. ie., sku, id, description, etc, the wizard with ask how you want those heading to appear in your store front.
The wizard will grab those pictures and put them where they need to be.