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if you want to use game characters then it's no problem. If you want to use custom characters the to play both on 1 controller you need to create them both on the same gamertag, if you want to play two custom characters on 2 controllers you will need to use two gamertags.
Any reason why you want to buy 08 instead of 09? I started on this one but haven't played for a while. I'm tempted to go to 09 for the speedier online play but at the min buying a new game and building a new custom character to full stats just for the online play seems like too much work. This board has been very quite since 09 came out so you might get more people about playing that one.