I think it is crazy that WP still expects us to upload pictures and other media all in the same directory.
After years of blogging that directory is an awful mess and retrieving stuff becomes a nightmare.
Why not giving the ability to create directories and put stuff into them as we upload a picture or a movie etc? Now wouldn't that be neat?
ImageManager plugin used to give the ability to do this simple thing, although it had other problems. Anyway , it doesn't work with WP 2.5... and as far as I know there are no plugins around that are that clever.
Bottom line, I think this simple enhancement should just be built in. What do you think?