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OK, good luck. I looked into the Roku soundbridge myself, but as I remember it doesn't play any music you actually buy at the itunes store (because of Apple's DRM), which was a deal-breaker for me. [Also--FWIW, why is line of sight a problem? You plug this into the Airport Express, not the...

In that case, you might look into the Keyspan remote. I don't have this (because I have Tivo, so I use Audiofaucet, which also has a nice interface on the TV screen), but I've heard it is a nice way of operating itunes remotely.

Get an Airport Express. This plugs directly into the stereo. Then itunes (on your Dad's Mac) can stream music wirelessly to the stereo. I have this; it works very well.