My solution was to create a set of auto playlists based on years and ratings as follows: Added to this is that I have to have separate playlists for my player's internal memory and its memory card. I use playlists to sync music to my player and I didn't want to have to manually work on playlists to keep them under 999 tracks. To illustrate what can be done, I had an issue with my Walkman where the maximum number of songs a playlist can contain is 999.

Advanced Auto Playlist: While the free version allows you to create basic auto playlists, Gold allows you to make extremely complicated playlists.As an example, I have my music files organized this way (everything in is a variable): Unlike most music management programs, MediaMonkey gives you full control when it comes to arranging the files in your music collection. If you update the metadata on a file it will automatically move it (if needed) to the new location on your hard drive.

Automatically organize your files: You can set up MediaMonkey to automatically arrange the files on your hard drive based on the rules you establish.

Among the features that only available with MediaMonkey Gold (the paid version) are (I will write what was mentioned on the website and then add my own comments, I apologize for the length of this post): Click to expand.I'm a long-time MediaMonkey user (I just returned to it to work with my Walkman due to Sony no longer supporting Media Go) and I will try and help.

Free alternative to itunes