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Hello Jason,
A clean installation of Windows Server 2008 x86 takes 6GB; an installation of Windows Server 2008 x64 takes 10GB. So for the 32bit version of Windows Server I’d go for at least 10GB and for the 64bit version you should have at least 15 GB’s. This all also depends of how much Server Roles/Server Features/Games/Applications you are going to install on the Windows Server partition.
I expect it will work fine if you install a game on 1 partition and create a shortcut from the other Operating System to it. If that doesn’t work, you can try to install the game from the other OS into the exact same location (so it will overwrite the files) and it will register itself in the registry and copy files outside the installation directory too.
Hope this answers your questions! 🙂
Arris
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