IMac Audio Routing, Simultaneous Built in & Headphone?

Hi there, First off im aware of soundflower, audio hijack etc...
I have a client, and that client has a new 20" iMac in a living room and wants to have the audio from the computer (youtube viewing...) sent to the TV while simultaneously keeping the audio playing out of the built in iMac speakers.
Maybe im missing something in soundflower or other apps but it seems that the iMac default sensing of the headphone jack automatically overrides any ability to do both.
Currently the TV is setup with a VGA cable sent from the minidisplay port and an audio cable in the proper audio ins.
The other solution would be to send audio via a USB device such as an m-audio product. But im trying to make it as fool proof as possible without creating enormous wiring clutter.
Could really use input on this ASAP. What am i not thinking of?
Thanks in advance for your time and help.

Saw this, wonder if it could work in conjunction with soundflower so the system knows to use both.
http://www.m-audio.com/products/en_us/Transit.html

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