OS X 10.8 or later. This script will look for an image file in the parent folder of each selected track's file--presumably its Album folder in which you have previously placed an image file of some sort--and apply the data from that image file as artwork for the track.
Export album artwork as folder.jpg to Album folder
Log playing tracks to text file
Enter text for the selected tracks' Description tag
Copy Artist to Album Artist of selected tracks
Edit a selection of iTunes tracks' tags in single window
Create a playlist of random Artists and set number of random songs back-to-back