Right after I posted this thread I saw the thread at How to update a large collection? where you mentioned beets which I had never heard of before. I’m very interested in learning more but as I am a windows user it looks like I’m going to have to jump through several hoops before I can get it up and running. I don’t plan on making any further to my folder structure until after Plex gets done re-scanning everything so I have a couple days to figure it out. There is a trick to fool the Plex scanner into scanning the artists by letter folders alphabetically when creating a library and I can’t make any changes to the folder structure until the scan completes.