It was just poorly designed I guess.
Thank god I wasn't the one who wrote the private messaging subsystem...oh wait, it was me. ;)
By the way, I'd like to upload an avatar but don't remember the limitations i.e. max. kilobytes/pixels?
Current limitations are GIF, JPG, or PNG at up to 640x480 or 500kb to upload. From there we'll resize down to 80x80. It looks like that resize isn't working properly, because I get a broken image in all cases. Chalk up another bug for the list. ;)