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Honestly haven't really looked at the Zune (I love my xbox, but c'mon, the Zune makes the H340 look slim and petite!), but as a general guide, if it uses a database methoid to sort music into artists/genres/etc, that'll be based on tags, and yeah, you'd probably have to go down the same path. Corrections welcome from anyone, I haven't looked around in a while.
I know a lot of people love that system, but even ignoring the issue of updating the tags, that sorting method still shits me to tears. I love my file tree, so I won't be buying anything that doesn't let you select straight from the folder structure. Personal preference though.
As for future iRiver HDD players, there's finally some good looking gear on the horizon, with a lot a cool 30-60GB HDD-based players shown at CES recently, but no idea when they'll make it to stores. I actually emailed iRivers importer in Australia today to see how long a wait it might be. Fingers and anything else you have crossed.
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