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Those little FM transmitters are probably not going to get you more than a few feet. Not a lot further than from the ipod to the car stereo. I've never used one so I could be wrong, but that is what they are designed for. Unless you used some larger powered transmitter, like for those home wireless music systems.
You could use a long cord spliced to allow plug in directly to your radio. You probably would want to figure out some way to plug in the ipod to a larger battery source, as the battery is small, and they typically use only a very small current to make the music in the ear buds.
Sound like a cool idea overall if the technical hurdles can be broached. You have to love the interface of the Ipod.
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