"... that I plan to use on my 360 which also has a copy and another 360."
What do you mean by that? You have 2 copies, one on a USB drive and one on your 360 of the same saves and Arcade games?
I'm pretty sure the question to your answer is no. I have a new Elite with a flash drive in it but I also have a HD in there. If you choose to save on one device you would have to manually copy it over to the other device if you want to load of the other one. I don't think the 360 has any auto-syncing feature.
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