Your extreme focus on efficiency and organization entertains me.
But...but...it's not just effeciency, and organization for its own sake... I need a way to get back into my music without making many sacrifices in other parts of life...
Why do you "need" to? What's wrong with your life now?
And it seems to me like you ARE making sacrifices in other parts of life when you spend so much time trying to fix something that isn't broken in the first place.
If you use iTunes, you could rank the songs according to how much you like them, and then listen to the "Party Shuffle" playlist and check the option "Play higher rated songs more often". I think this would solve your problem of wanting to listen to your favorite songs most of the time, without leaving out the other songs that you might want to listen every now and then and not neglect.
Or you could stop worrying about something like this. But I doubt that will happen.
TSM seems to have pinned the tail on the donkey. can i help you stop worrying about this? in exchange for your entire music collection, i'll rip it to iTunes for you. (though do expect this process to take several weeks... i had this on my agenda to do, when i'd borrowed a couple of those big books last year, but never got around to it.)
I mis-spoke, I don't *need* to, I'd *like* to get take better advantage of my music collection... which I'm sure if I added up the cost, reflects multiple thousands of dollars over the years.
Life's too short for B-sides.
(except for those hidden gems, but hey)
Is there a system that's good at letting you tag songs, ala flikr? It seems like that might be a more flexible categorization system than playlists.
Life could also be too short to spend organizing music to trying maximizing the benefit. . .. =D
It's not quite as obsessively geeky as you're trying to make it... I just tend to write about it at greater length...