Yeah we have separate Xbox accounts.
We do however game share. That means when one us buys or downloads a game the other console automatically downloads it also.
But that really doesn't apply this time because the game was free for gold so we both would be able to have our own copy anyway.
I also even have the disc version of the game (Played the mess out of it when it came out) so just now trying to get back into it since I can now play with my brother (plus other friends since it was free)
I'll try again today and see what happens. May restart my router and what not and see if that helps.
Thanks for the help so far everyone! I'll let you know how it goes.