i rigged up one of these systems
http://www.htd.com/whole-house-audio/advanced
its a true whole home audio where you can independently select sources in each zone. each zone has its own amp. Just select the source at the keypad (or use a harmony the keypad has IR) and you are good to go in any room.
Threw an apple TV back in the rack, and he can control the playlist from anywhere on his iphone.
it requires that you run cat-5 from the rack to each keypad location, and the speaker wire runs can go directly to the rack (instead of to the keypad).
You can hook up an ipod anywhere there is a keypad and it becomes a new source as well.