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If you know software which creates two virtually connected COM ports in Windows, you can configure the two WinUAE instances to use these two ports.
It's definitely possible to connect two WinUAE instances through a physical connection on a PC with two COM ports which are connected to each other with a nullmodem cable.
There might be another problem, though, because only the active instance receives input. The other instance can watch, but not act.
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