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I have a Rio 600, which is the same generation as the 800, and it works great with iTunes. I never even had to put the CD that came with the Rio in my computer. It worked with iTunes right out of the box. However, once you put songs on the Rio, you can not play them through iTunes or otherwise copy them back to the computer. This is to prevent the copying/ spreading of copyrighted materials. iTunes rules! Thanks Apple!
I'm hoping Apple will add more for the newer models that come out. Although that Rio600 is a good deal at $170, but an even better deal if you get it through the "college bound" deal at: