I've used ppctunes (http://www.pocketmac.com/product.php?id=5) for many years on and off. works pretty well and syncs through ActiveSync.
i also just saw this Pocket Tunes player. seems pretty extensive and says it syncs with your media player playlist as well as itunes. but you're looking at $35 insteal of $9
http://www.mobiletopsoft.com/multimedia/getproduct.php?pname=Pocket+Tunes+Deluxe+4.1.0
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