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I guess I don't understand "cleansing" plug-ins. As far as I know even Itunes has given up on DRM. It downloads in AAC, but if you highlight a song and right-click it, you can make an MP3 copy of it. Amazon has always been DRM-free, as far as music is concerned.
As far as organizing your music library and playback devices, converting formats, etc., I've heard very good things about MusicBee, but I don't use it.
I use the free version of Winamp for playback, but it's too limited to do much else. The paid version is supposed to be pretty good.
Basically, I manage my music (a 2 TB external HD, half full of WAV files) manually. I have a handful of programs to rip, play, convert, etc.
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