Nevermind! It turns out that none of the squeezeboxes were able to wake up my iMac. After some investigation, it turns out that the wireless WOL feature requires the server to be registered with Bonjour. Apparently Bonjour support was removed in 7.4 (?). I was able to run a program called Lingon that let me set up a service that automatically registers the Squeezebox Server with bonjour. Now my computer will automatically wake from sleep when accessed by any Squeezebox. Note: this is apparently an Apple only option, in that you need an Apple Airport Extreme/Time Capsule and compatible Apple computer.
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