This may be a good feature to consider for the next release. One of the things that drew me in to check out K2 was the whole idea of auto image re-sizes to five or six different sizes. I thought this would be a good feature to recommend to my clients who are squeamish about resizing and uploading images by ftp. If you could set up a routine where people could drag 10 images into the K2 Media manager, have them re-sized into appropriate folders, I think you would have a feature that could be really useful to a lot of people who have been assigned the task of CMS.
One by one, where images are sent to obscure folders with odd names, outside the view of Media Manager, just doesn't help these people much!
I'm just say'n