Well I stumbled upon the answer! I was standing in the living room talking to my wife about what it was I was trying to do, and my 10-year old son mentioned that on HIS macbook, in HIS iTunes, he was being prompted to connect the remote. But he had no idea what it was, so he was ignoring it.
LOL.
So, the moral is that other machines on the network can jump up and intercept the request. I shut his down, and bang, worked like a charm on mine. Thanks for all the help.
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