First step may be to find a media client that he would be comfortable with. Slim Devices (now owned by Logitech) has the SqueezeBox, which a lot of people really like. There is also the Sonos system, although it is a bit pricey. I've got a Roku SoundBridge, but it is an older platform and not especially impressive in the first place (at least in my mind). There is also Apple, who have both the Airport Express (no local controls unless pops carries an iPhone) and the AppleTV. Once you find the client you like, it will impose some limits on what server app and hardware you use.