I have a DICE Silverline with a 5g classic & love it. I used to have it in the trunk but have bought the specdock as I found controling the ipod from the radio was clunky and too slow. The classic goes into hibernation every 14 hours-so I had set an alarm for every 12 to get around that problem. It sounds like you would have to do that much more frequently. It worked, but it would also reset the ipod-so I would never be able to continue on with my music where I left off. I'd suggest routing the cable or getting the dock to put the ipod within arms reach. If it's asleep you can simply grab it and use the hard buttons to wake it back up.

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06 4.4i
01 330cic