Directories are not impossible, I'm just not sure how to make the interface for them look good and work well. It's more a UX problem than a coding one. I would love some suggestions/sketches/wireframes to improve the editing dashboard to enable this. Please send me an e-mail if you have any ideas here.
Yeah I agree it's not a simple suggestion on my part. I'm by no means an expert on UI/UX and so I'm a bit out of my depth here, but I'm hoping that someone can suggest a design that lends itself well to this. In the meantime, while it's way more complicated than what you're going for, dropbox's upload interface might be worth looking at.
