I agree with dave360, i too despise iTunes. Granted if you're looking for a seamless combo between your music software on your pc and your player iTunes and an iPod is still tops. The Zune software is pretty poor and WMP is horrible. My last player was a toshiba gigabeat s60 (basically what the Zune was built off of since Toshiba made the Zune for MS). It was a MTP/Playsforsure device so you had to use WMP or some other 3rd party software to get your music on the player. One word: Hassle. I used MediaMonkey (i've since switched to J.River Media Center, the best i've used yet) and while it was better than WMP, the fact is that these programs aren't designed towards any one DAP whereas iTunes is made for the iPod and vice-versa. Until MS makes the drastic improvements with the Zune software, people used to that experience don't have much of a choice other than an iPod.
Honestly though, if you wanted to not fight with the machine to get your music on the player, don't pick up an iPod or a MTP player like the Zune/Creative Players. My first DAP was a iRiver H320 and all i had to do was go in explorer and drag my root music folder over to the H320 (which was an MSC device so it showed up as a Hard Drive) and boom the file structure was duplicated on the player. A few button presses and i could have the artist/album/genre view if I so desired. I don't have a player now because i'm waiting for Cowon/iAudio's followup to the X5, the X7. Cowon's players work the same way as i described above. You can also use these players with software, sure, but the point is there is no obligatory software.
A good site for anyone interested in knowing more about DAPs (thats Digital Audio Players, because they play more than just mp3s guys) check out Dapreview
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