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I use an iRiver T20. I want software which shows me simple images, like folders in Windows, of the albums in the T20 and images of what I have in my computer file of MP3 albums, so that I can easily transfer and delete content. Both the iRiver software and Windows Media Player make the business much too complicated, for example by showing me every MP3 track in my computer. I look at players like the new Nano iPod and think, surely there's freeware which can make it this easy to handle music files?
if you just set windows media player right, and have your music library/ies in there, and get a good album cover downloader for wmp, you should be able to sync your iriver without hitches. besides, it's a rare occasion that you sync your device with a computer anyways - might as well rip off the band aid once than endure it for weeks and weeks.