The only potential problem is if he has never connected to Live before, it'll make him do the system update before he can play on Live, which may or may not affect his chipped 360. Chances are if it does affect his system, it'll just remove some of the affects the chip has instead of bricking it, but it's something to be aware of.
I think with the previous 2 system updates for the 360 they have been bricking modded consoles. I remember reading it here, problem was is that it was bricking systems that didn't have a mod, so MS had to replace those consoles. I would be very carful. Your friend might just loose his console just for connecting it to live, along with the subscription.Send it in if it bricks and they'll laugh, won't get a replacement.
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