Jedi QuestMaster: I was leaning towards this direction with custom genres, but I wasn't sure where to cut things off. For instance, I can have two tracks that are both very calm and relaxing, but one is very upbeat, the other is much more dark and morose. Or I may have music with a desert theme to it that doesn't blend as well with a lot of my other tracks, but is too slow / fast compared to other desert tracks. I'm impressed you can get yours down to just 5 categories.
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Yes just tag your files properly. Either the widely used genre field, or use/or add custom ones ("mood", "type" or whatever you want to call them). Once everything is tagged, play them back with a player with nice database capability and voila. That's how I do it and I'm happy with it.
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Exactly, this is what I've been attempting to do, but I don't know WHAT criteria to use. If I get too many custom genres it's not really practical, but too few and you get a lot more mismatches with music. What custom genres do you personally use for your music?