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Hi, the only benefit you may find from using a different software version is the older software (v1) which allows more indepth editting features, although your Zune will have to be downgraded also to v1 otherwise it will not work. I recommend using the latest software v2.3, and editting your music tags and creating smart playlists etc (the features that are currently lacking depth in the new software) using Windows media player or another tag editting program. You mentioned Media Monkey 3, and that might do the job of editting tags very well.
Sorry that i posted this here, we do not do personal Instant Messaging for support threads unless there is a serious error.
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