Can I transfer my original Xbox save games and downloadable content to the 360 hard drive?
At the moment, the answer is “no” unfortunately. Microsoft have officially stated that it will not be possible despite rumours that you may be able to network the two machines together to copy the data. It might be possible to copy the save games with a third party accessory such as an Action Replay or MegaXKey but this remains to be seen. Likewise, there is no way to transfer downloadable content either. This means that the premium DLC packs for Project Gotham Racing 2 and so on must be downloaded again. As you can transfer your Live gamertag to the 360 it might be possible to download these packs again without re-paying but, again, this is unconfirmed. For now, expect to have to download again and possibly purchase again on the 360.