Looking for a simple answer to whether or not I will have to buy a second Xbox Live membership for both my son's Xbox 360s one will be at my house and the other at his mother's???
its up to you wheter to buy gold membership. I would just to enjoy the service and have free games for having gold. Dont forget if your son has silver he wont be able to play online with other users.
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If he's using the same account on both consoles, then no. The subscription is tied to his account and not the console.