While developing the Foliopress WYSIWYG we decided to create the images management on the basis of Kae Veren's excellent KFM file manager. While we are totally happy with how KFM handles the images itself, we were unable to work with images uploaded via ftp.
Uploading images one by one through an image editor is fine, uploading twenty that way is annoying. One of the reasons to prefer WordPress over Typepad is that you do have direct access to the server via ftp. So this was clearly not acceptable. It wasn't even possible to change the file ownership of httpd via SSH (without root permissions).