After doing a little more searching I figured out what was originally triggering and causing this error message to show up in the first place.
The important thing here is not why did Doug not have his folders Chmodded even though the answer is I forgot to before trying to upload a file, but how to get this fixed for future posabilities of this occuring with someone else.
For anyone wishing to duplicate this problem to try and find the cause of this, chmod your "files" folder and everything under it back to 755, and delete the user ID folder for the user id your logged as. Such as for the Admin ID which is "Folder "0".
Then try to upload a file, you should get the contact the webmaster error message at at the url of /gallery/upload.php.