I've just spent some time trying to delete files from Toodledo that I had uploaded some time ago, just to make the selection of a newly uploaded file easier. I didn't notice a way to delete multiple files at once. It was quite tedious to click delete, then confirm, for every file. I ended up giving up. If there were some mechanism for file management, I suspect that many users would reduce the number of files in their account. Right now, its much easier to let them accumulate.