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Are both games emulator versions of them? Because I think someone posted on here, at some point, that you can do it, using a LAN, if I remember correctly.. but then again, I could be completely wrong.. ^^;;
Yes. If it's a game save then yes. However you can't really trade Pokemon from Emulator to Emulator in your PC [I forgot but I remember trading in NDS emulator. O.O].
Yes this is possible if you are connected on the same LAN. So you could have the emulator on both computer and simply run them as required, just like you would if you were to trade across handheld consoles.
But an IP address is required for both computers I think. Check up on this, go onto your help search on your PC/iMac. You'll be able to see the IP addresses through this way.