If he paranoid? Wanting to use an iPod and "absolutely refuses to use anything that relies on the internet or wifi when it comes to audio" seem to contradict each other, unless he plans to rip his own files.

Bluetooth can work, but the building would dictate that- I have used the Miccus BT receiver and the range is excellent, even though the signal has to pass through three concrete block walls to go from the handheld device to the receiver (shortest physical path) in a school gym with a full basketball court. This Miccus piece can be used as a transmitter or receiver, so the system could have one transmitter and several receivers, but I haven't used it in that way, so I don't know if latency would be a problem. It's only about $50, so buying one for testing won't break the bank.