Unfortunately, I don't have a definitive answer to your question, but it's a brilliant idea if it would work. The database contains those attributes but it's doubtful a smart playlist could be derived without a lot of manual labor. I will also keep watching this space for an answer.
No, iTunes will not do this for you. There might be a 3rd party script or application to identify such tracks.
Finding missing artwork is easy enough, just change your library to display in grid view or coverflow and look for missing artwork. You can also use list view if you expand the artwork column (click on the left arrow in the header over the left column).