This may come as a surprise, but I’m a bit of a pole-in-the-ass organizing nazi. I’ve spent over the last year slowly tagging my music collection. Way back in the day I used RealJukebox as my media player of choice, it was basically iTunes before iTunes existed. The thing I liked best about RealJukebox was the ability to give ratings to the songs you liked and build playlists that paid attention to those rankings.
Yesterday I managed to finish rating every song in my library and can just let my smart playlists determine what gets shunted over onto my shuffle. I still need to get the release year for many of the songs, and the lyrics for all of them added, but thankfully I have a program that will do most of that for me.
My digital music collection is in tip-top shape, I ended up deleting much of my Bowie collection, I still have the discs, but the only stuff I ever listen to is Ziggy Stardust/Diamond Dogs era. Now all I need to do is track down a good record player and get some decent speakers for my physical music collection. Too bad Play it Again Sam closed down.