Hey Cheesypoof,
Thanks for such a quick reply.

I found that workaround on the forum last night, when I came back after looking for a CKeditor solution. What I found there seemed like it was really about internet embeds vs uploading to the server the editor is on. A search for 'video uploads' on the forum brought me to your solution. CKeditor also looked like I'd need to build a whole new version of the editor rather, than simply add a plugin to the existing one.

I hope I am wrong about that.
I may go with file workaround, or I may try and see if I can implement 'Media' since it seems all of 'Images', 'Flash', and 'Files' are already implemented. I like the idea of doing it 'right', espcially since Couch by default already makes the directory. If you can tell me that there is a reason that it is really hard

, and that is why it's not already implemented, I'll trust you, and go with the workaround. Otherwise, I like Couch enough to want to dig into it more anyways, even if this is really digging into CKeditor mostly.
From some of the forum posts, it seems like old Couch may have given access to the top level 'uploads' directory from which someone could go anywhere beneath it. If that is the case, may I ask why it was decided to do something so much more restrictive? Or, is that just a CKeditor issue?
It seems strange to me to have the uploader be so restrictive in the directories that it makes availabe. If people want to be unsemantic in where they put their assets why not let them,

vs. decide that flash ssets have to be below the flash directory, image assets have to be below the image directory, and similarly for files and presumably media. I'd separate the latter into audio vs video myself if I just had access to uploads from the top level.
If I assume tmp is a working directory, why does media exist, but not have an uploader for it?

That's my 20 cent question?