uploading files... managing lots of files.

If you are using acts_as_attachment (or attachment_fu) to upload the
files then you can use this strategy to create more directories.
http://blog.spotstory.com/2006/11/10/extending-acts_as_attachment/

If not, I would recommend using attachment_fu to do uploads.

-bakki

Or just use the latest version of attachment_fu, it does that by default.