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I know this is a dead thread, but I can say with 100% certainty that it does. All music--drm'd or not--is subject to the 3x3 rule. Currently, the only way to get around it is to use a program like ICHWM to package songs you think you might want to send. When the person gets home, they can sync pictures (which aren't subject to the 3x3 rule--go figure) to their computer, and unpack.
That's the best solution I've heard so far, until MS pulls its head out of its *** and does something about it (that surprisingly the other wifi players have been able to do since launch).
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