Hi Brad. I am using a fairly old version of Winamp but here is how I make playlists. If I want to play more than one track at a time, I open Winamp then press letter L then shif-tab in to the folder where my songs are located. Select the ones you want then press Enter and they should start playing. If you want to create a playlist, you might press Alt+E then control+tab to open the playlist editor. Press letter L to add tracks to the playlist. Add as many tracks as you like even if they reside in different folders. You can move from folder to folder using either shift+L or just backspacing to the various folders. You can then save the playlist with control+S. Note: you can obtain a list of winamp keystrokes specifically for the playlist editor by pressing insert+W while in the playlist editor.
Hope this helps.
Pete

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