I was thinking exactly the same. Instead of a Pi I would take an Intel NUC (better performance and more important Windows running on it to run ISBoxer).
Now instead of targeting a running World of Warcraft instance ISBoxer is giving it's output to an output device which is emulating a keyboard via USB to another device. From a technical point of view maybe taking keyboard controller and put some logic behind it instead of the physical keyboard so the target machine is recognizing a real keyboard.
I think five computers would be the easiest solution (or VMs) as I am not aware howto assign a keyboard to a specific application when multiple are attached to one computer.
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