Jimmy-
We do need to be careful about "fair use", because it does raise some potential issues for some re-users.
The truth is that since I created [[Wikipedia:Fair use]], to develop a process to sort out fair use images where we can come up with free replacements, nothing has changed. People are still uploading fair use images of actors, politicians etc. where I believe it would be possible to obtain free images.
I do think we need to put some more emphasis on the process detailed on [[Wikipedia:Fair use]], and possibly be a bit more strict in deleting images which do not comply with that process. However I think letting sysops delete images without due process is not a good idea. We just need to develop a better feel of what is acceptable and what is not. As long as long-time regulars keep uploading questionable fair use pictures the newbies can't learn the boundaries either.
Personally I think that the more information content or historical value an image has, the easier fair use can be justified. I wasn't very fond of seeing a promotional poster from "The Passion of the Christ" on the frontpage, though, and not just because it's a pornographic movie.
Regards,
Erik