PlayIt Live and PlayIt Manager are great for loading existing categories from another piece of software into PlayIt. Just put the music files in separate folders per category, and then suck them into PlayIt while instructing it to assign that folder to a particular category. BUT: once you've got all your music loaded in and you want to start moving music between categories, things aren't so easy. If you want to avoid duplicates between playlists, you have to remove the track from category A and then add it to category B. A drag & drop-style functionality (think: files in Windows Explorer) with a button to listen to the song / scrub through it would be great for music directors who want an easy interface to manage the library, build season playlists, etcetera. For inspiration, you might look at the 'BaseBrowser' utility from good old Dalet 5.1, if you can get a hand on that. It was ugly as heck, but it worked like a charm!