If he's starting games, he can't possibly have the wrong version if he's playing via ICO...if it's through direct connect then idk....
If there was a checksum difference, you wouldn't even be able to join the same game lobby, regardless of whether it was ICO or direct connect...
W8 is not going to be your problem either, at least not directly....depending on how it was installed, I suppose it could have affected the driver for a network adapter, but you would probably have noticed something wrong by now that affects something other than Sins MP....
Making sure your connection is solid can help...make sure no one is torrenting...
We are talking about a desync, right? Not a disconnect?