Well, I've gone the DOS route and I'm not sure if you could do something like this in winamp, but I think it's worth sharing.
http://www.mp3car.com/ubb/Forum3/HTML/000262.html
Basically, I have all my tracks in folders/subfolders based on artist then album. The program I am using loads all the MP3s on the drive and then can step through each folder. Since it loads them alphabetically (DOS) I just use the skip folder button to advance by album and the skip track button to advance by song. I can also dial in a track directly (ie. 1388 jumps to that song). Since it's alphabetical, it's pretty intuitive to guess where a track is, or at least get close to it, and then skip up to it. I only use playlists for specific compilations. It's also good because anytime new tracks are added, I don't have to make a new playlist or change anything around, they're automatically put in the right spot.



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