You might as well just get an ipod or Creative Jukebox - easily carried on the person whilst on shift.
As for the transmitting, you could go for the walkie talkies and wire up a set of pmr radio's (FRS if you're in the states). Those little radio's are pretty good quality transmission-wise and work well in built up areas, but I think continuously transmitting music is illegal as far as I know



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You might want to bite the bullet on this one. I have 
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